My family’s from a farming community in Haiti. When my parents moved to Boston in their mid twenties, they had children pretty immediately. At the time, me and my 3 siblings lived in mostly illegal communities. It’s interesting because you don’t know that you live in that sort of community until you start meeting Americans who live a bit differently. We were very “green.” We used buckets of water to bathe instead of running shower water. Our front lawn was a garden. My parents were not accustomed to refrigerators so they became a pneumonia scare in our household. In fact, to them everything caused pneumonia and everything could be cured with a cup of tea.

“At the time, me and my 3 siblings lived in mostly illegal communities. It’s interesting because you don’t know that you live in that sort of community until you start meeting Americans who live a bit differently. We were very “green.” We used buckets of water to bathe instead of running shower water.”

Growing up I was a very, very inquisitive child. I constantly asked questions, and context clues meant everything to me. It always confused me how people would do things without asking why? My parents had a lot of difficulty answering my questions due to the language and culture barriers. They encouraged me to read more, with the mindset that the bigger the book, the smarter I would be. The older and dustier the book, the smarter I would be. The harder the cover, the smarter I would be. Really interesting context when you really think about it. I eventually started reading dictionaries and encyclopedias, searching for answers.

When I was 11 years old, I noticed an advertisement on the back of a magazine with the words, “Do you have questions?” I took this as a sign to get tons of questions answered. I ran away from home in search for the magazine headquarter, which happened to be in Boston. Upon arrival, there was a massive exchange of questioning and they soon realized that I had no idea what my address, phone number or birthday was. They sat me in front of a computer and taught me how to play solitaire until my mother eventually found me. My question started to shift from day to day questions, to questions around machinery, interface and context. That began my path into the world of User Experience.

How were you were first introduced to Computer Science and/or UX?

Well my mom brought me back to the magazine HQ the following Monday and told me not to tell my father. In our household, the girls were very protected. I was supposed to go to school and get home as quickly as possible. I was not allowed to make friends. But my mom was a bit of a secret feminist and encouraged me to outsmart the boys and teach her all I had learned in school. Staff at the magazine were pretty impressed by me and encouraged me to continue learning about technology. They eventually were able to take me to a place called The Computer Clubhouse while my mom worked. The Computer Clubhouse was a free technical after school program designed by professors and students at the MIT Media Lab. They targeted inner city kids as young as 8 years old and taught us how to use industry level technical tools. They believed exposing underrepresented individuals to a number of technical skills early on, could help bridge the digital divide. The additional blessing was the frequent visits from people of color at MIT pursuing PhDs in Computer Science and Media. At age 12, I played with actuators and sensors. I also was introduced to coding and programed the very first driverless lego cars.

When I was 14 years old, I ended up in foster care due to a variety of reasons including domestic violence and cultural friction. I ran away a lot and was very depressed through those middle school and high school years without my family. Despite all the personal struggle, I always found my way back to the computer clubhouse. I had all these cool tech skills and loved teaching. By the time I was 17 years old, I was teaching girls how to make their own web pages and remove the proof watermark off photos they had not yet purchased from school. I shortly became an assistant manager at the computer clubhouse, a Tech coordinator at the local YWCAs, the Museum of Science’s technology courses instructor and an IT risk auditor at Harvard University all while I attended undergrad.

“When I was 14 years old, I ended up in foster care due to a variety of reasons including domestic violence and cultural friction. I ran away a lot and was very depressed through those middle school and high school years without my family.”

Despite all of my technical ability, I was too scared to pursue a computer science degree. I believed it was a man’s job despite the fact that I was already doing it. So I went to school for Information Systems and sociology while teaching computer science on the side. When I was in my junior year at undergrad, I decided to take a java course and was pleasantly surprised. I already knew how to do a lot of this stuff. The wave of questions began again. “Does that mean I can code? What’s the point of the degree? Do you need a degree to be a coder? I’m confused. Can you just learn this stuff on your own? Are you not an engineer unless you learn to be engineer in school? Are Haitians who build bridges without degrees not engineers? Wait, what do I do with this sociology degree?” Sociology was the field that touched my heart and technology was the field that stimulated my mind.

I took several psychology classes and professors really felt that it might be my calling. But I could not imagine humanities paying back school loans. By the time I graduated I decided I wanted to do it all. I took to the Google search engine and typed in all my passions, “sociology, psychology, computer science, engineering, hands on, love, forgiveness…” And two fields popped up—human factors engineering and human computer interaction.

How did you make that transition?

I went to Michigan to pursue both degrees: a masters in human computer interaction and a PhD in Human Factors Engineering. It was EVERYTHING. I had somehow found fields that connected culture, engineering, empathy and compassion. And I got to doodle all day to top it off. The wonderful thing about the Computer Clubhouse is that it was funded by Intel. I was able to work my way through the network and worked as a human factors engineer while attending grad school.

At Intel, I met an amazing woman and Intel Fellow known as Genevieve Bell. Genevieve was an anthropologist and a human factors engineer who focused on cultural practices. That was the moment my entire life started to make sense. I had grown to a place where I truly appreciated cultural differences and empathized with day to day struggles of Keeping Up with the Silicon Valley Millennials. I knew I could help make life a little more easier. I wanted to help design products that showcased empathy. And I knew it was my destiny.

Walk me through your work and what you’re working on now.

I eventually went on to work on international projects as either a developer, engineer, or designer across many industries; from government to medical devices to worldwide leaders in IT. Today, I continue the great work at Google in the consumer operations space. I get to measure my work impact globally. I am also launching a personal global passion project called Tech Social Impact Conference in the first quarter of 2017. The conference sparks conversation about developing intentional awareness in product development. In Silicon Valley, we get to see how design and technology can provide social and ethical benefits (and sometimes consequences). I’d like us to share principles and approaches to contribute to a better tomorrow for the next billion users.

“Another goal I am working on is changing the way we do research in the tech industry. I want to make that our research takes into account social and economic backgrounds. Are we designing towards the average income in the United States? Are our studies mix gendered? Have we paid attention to accessibility? I’m all about making a difference in this world, and I know I am in a very privileged position to influence that change.”

Another goal I am working on is changing the way we do research in the tech industry. I want to make that our research takes into account social and economic backgrounds. Are we designing towards the average income in the United States? Are our studies mix gendered? Have we paid attention to accessibility? I’m all about making a difference in this world, and I know I am in a very privileged position to influence that change.

It’s so cool to see all of the ties to your work from your childhood to now. What parts of your work as a researcher really activate you? What do you love the most?

I get super excited when I get in front of people, and I mean real people (no offense to Silicon Valley folks), I’m so passionate and empathetic towards the people I design for. When they’re in front of me, I want them to be comfortable. I want to hear their truths. I want them to tell us how we suck. I want them to know that I appreciate it, and I want to make a difference for them.

It’s one of those things, when I’m in front of somebody, when I’m in front of an actual human being, to know that, “okay, maybe you don’t have the same technical abilities as I, or maybe you feel a little scared, but I’m going to change this for you. I’m going to make this easier for you.” It empowers me. I just ran eight studies today with folks, and every last one of them said, “I’m not really good at tech. I feel like I’m messing up.” I say, “This is exactly what I need. And you’re perfect. I need you to tell us everything we could be doing wrong, so we can fix this for the lot of you that may feel the same. It’s not about looking for a tech genius. If that was the case, we’d make no money. And we need you to keep paying us, so I need to know everything that makes you cringe and what makes you happy.”

I’m curious to know, in your eyes, the potential of research in tech and what are the problems that we should be solving with research? What are we not doing to approach this correctly?

The reason research is so beautiful is because it’s data. When folks try to say “This is how I feel this should be designed,” I can say “Well, 80 percent of people we tested won’t go through it.” Or when I hear, “Can these users really speak for the rest of the country?” I’ll say, “Well, you know there’s this little thing called sample sizing. Pretty dope stuff.” It’s just really empowering to influence people with research.

“We’re not building for just ourselves anymore. We’re a global society. Everyone is using our technology. There is a huge culture shift and focus on design for the next billion users and I think it’s a great direction. And guess what? Sometimes design requires contrast. That means we may need to have different people seated at the table to help us design. You might just have to hire that super poor person in the village you’re building for. It might just mean spending time living in the communities you are serving. It might mean better design for our products due to diversity of thought.”

The problems we should be solving for is cross-culture design. We’re not building for just ourselves anymore. We’re a global society. Everyone is using our technology. There is a huge culture shift and focus on design for the next billion users and I think it’s a great direction. And guess what? Sometimes design requires contrast. That means we may need to have different people seated at the table to help us design. You might just have to hire that super poor person in the village you’re building for. It might just mean spending time living in the communities you are serving. It might mean better design for our products due to diversity of thought. I see nothing but wins when you consider research as a primary practice to help think more critically about the ethical and societal implications of the technologies we design in this world.

Let’s go back to your personal narrative. Tell me about some of the bigger roadblocks and struggles, in your career that you’ve had to overcome.

Being yourself in a world where being yourself seems wrong. In the last year mentors have been telling me that I can fully be myself and be accepted. I never believed that. It wasn’t because no one was telling me I couldn’t be myself. The culture just didn’t seem to want me. So I faked it. I fake laughed at jokes, I fake pretended to see movies I hadn’t seen. I faked drinking beer when I thought it was disgusting. I tried to be a bro when there’s not an ounce of bro in me. It’s pretty draining because I would spend 80 percent of my day pretending to be somebody else­­ or I’d sit in silence when I’m not a silent person. There’s some parts of me I just cannot hold back, like when I disagree.

“In the last year mentors have been telling me that I can fully be myself and be accepted. I never believed that. It wasn’t because no one was telling me I couldn’t be myself. The culture just didn’t seem to want me. So I faked it. I fake laughed at jokes, I fake pretended to see movies I hadn’t seen. I faked drinking beer when I thought it was disgusting. I tried to be a bro when there’s not an ounce of bro in me. It’s pretty draining because I would spend 80 percent of my day pretending to be somebody else­­ or I’d sit in silence when I’m not a silent person.”

It’s still a work in progress but I’m trying to be unapologetically myself no matter where I go. I’m now about 70% myself which is pretty amazing. I would never have imagined that. And I have experienced so much good because of it. A mentor once told me that the Valley was a strange enough place where I could fit in and be appreciated for my differences because everyone is so different. Another mentor told me, “I don’t know if you know this, but when computer science first came out, it was considered a woman’s job. It was like secretarial work. But all of a sudden because somebody told us women we can’t do this­­ or that— that perceived ability has disabled some of our powers. It’s insane. And we as women are fully capable of doing any and everything in tech, if not better.” These words definitely helped.

When did your attention start turning towards educating minority communities?

I’m very passionate about that because someone took the time to show me that I wasn’t forgotten and look how far I’ve gone. And it’s important to know that it also took someone that looked like me. So I serve that truth right back.

I also truly believe this—if you want to hire somebody, look at their story. The story matters to me. That’s how you find out actionable potential. That’s how you know that you can take this kid off the street, show him a few lines of code, and all the sudden he’s the inventor of a killer startup. It’s about finding folks that are hungry. So I set up the environment, and the folks who are hungry, come to eat.

“If you want to hire somebody, look at their story. The story matters to me. That’s how you find out actionable potential. That’s how you know that you can take this kid off the street, show him a few lines of code, and all the sudden he’s the inventor of a killer startup. It’s about finding folks that are hungry. So I set up the environment, and the folks who are hungry, come to eat.”

How do you think the combination of your background and your life experiences impacts the way that you approach your work?

Everything I’ve done has been because of experiences I’ve had. At one point I wanted to prove my value because I felt tossed away by the world. Now, it’s about making people know they are valued and impacting the world that way.

Last question. What advice would you have for young women, young people of color who are really hoping to get into tech but just don’t know where to start?

Look at several LinkedIn profiles for individuals who are in the career you want. Write down all the things that interest you and the common themes/skills. Teach yourself those skills. Put said skill into practice. Slap new skill on resume. Rinse. Repeat.

The majority of the things I know came from tinkering, searching for free education online, and application of that education. Don’t believe the hype that you have to be in school to learn new things. Now I don’t mean drop out. College is awesome. Go to college if you can. What I mean is that you can teach yourself almost anything these days. if you allow for a little discipline. What kept me motivated was knowing that the short term sacrifice of taking the time to learn something on my own, was going to lead to longterm rewards.

“Look at several LinkedIn profiles for individuals who are in the career you want. Write down all the things that interest you and the common themes/skills. Teach yourself those skills. Put said skill into practice. Slap new skill on resume. Rinse. Repeat.”

And please, don’t be like me for the majority of my life and not ask for help. The world is so much better when you stay open and vulnerable about learning through others. Lastly, sounds cliche, but no such thing as a dumb question. Get your education on.

I come from Seattle, Washington. I was born and raised there. My parents were a typical blue collar, working class, immigrant family. They made tofu for a living, and so I grew up in a world where soybeans were everywhere. We sold the tofu to two kinds of customers: regular folks like teachers or gardeners, or to businesses like restaurants. And it was very hard work, working all the time, waking up early in the morning ­ two o’clock in the morning ­ working to six at night. It was pretty intense, but I learned how to work.

What did your parents expect of you in term of a career?

My mom’s the third generation and my dad’s first. They just wanted us to get to college somehow. That was just a dream, because both of them hadn’t gone to college. My dad didn’t go to high school.

When did you first feel any inclinations towards tech or design?

I was lucky to have been born in the era when the Commodore PET came out, which was a little computer. I was also lucky to receive the benefit of the civil rights work in the 60s. Seattle was de­segregated. The people on the poorer side of town were bussed to the richer side of town. I was in the poor side of town. I was bussed to the rich side of town and they had this computer in math class. That’s where I found my first computer in the 70s.

Then you ended up going into software engineering as a student, correct?

Yeah. It was really my parents’ dream for us to go to college and it was either Harvard or MIT. My older brother didn’t get into Harvard, so he was considered a failure [chuckles]. So I said, “Well, I’ve got to get into MIT,” and I got to MIT and studied computer science there.

“If you connect your understanding of technology with an understanding of the history of art, you can do something new. When you do something new, it hurts because nobody likes what you’re doing because it’s different. I think our inclination is to be afraid of that pain.”

When did you become interested in design and then the integration of the two?

Well I think as a child I was said to be good at math and art, but my parents would never tell anybody I was good at art because they felt that couldn’t get you a job. I was “good at math” is what they’d always say. I loved drawing. I loved thinking visually. When I got to MIT, I tried to defect. I discovered this department called “architecture.” My dad figured out what I was doing so, “No, no, no, no, no. You’re not going to be able to feed yourself, so computer science; go back there,” kind of thing. But I used to go to the library at MIT and I would find these books on design. At the time I was probably one of the best icon editors on campus at MIT. Computers were just becoming visual and I was the guy that could make good icons. I thought I was really good at it. Then I found this book by Paul Rand, the graphic designer, and I thought, “Man, he is so much better than I am at this stuff.” [chuckles] That’s how I found the field of design.

Such a huge part of your work is combining tech and art and exploring the integration of the two. When did this feel like a focal point for you more than just doing the work that’s assigned to you?

That’s a great question. I forget all the time that I cared about that, if that makes sense. I’ll be waking up and saying, “Oh yeah, I care about how those two connect.” Then I’m off forgetting everything. “Oh yeah, I care about that.”

I guess it’s because I was lucky in the 80s and 90s to see how, if you connect your understanding of technology with an understanding of the history of art, you can do something new. When you do something new, it hurts because nobody likes what you’re doing because it’s different. Each time you touch that third rail, you’re like, “Ouch! I don’t want to do that. I want to be a regular engineer. Or, I want to be a regular artist.” So I think our inclination is to be afraid of that pain. I’ll come close to it and I’ll go away from it [chuckles] and I’ll come close to it and then go away from it. I’ve always been having this problem. I’ll be in art school, I’ll be in engineering school, I’ll be in Silicon Valley. I’ve always been running from and towards the third rail.

“I’ve always experienced push­back. In art school, I remember in the early 90s my conservative design teachers told me, “Stop making things move on the screen. That’s not right.” Or being at MIT, and my engineering teachers telling me, “Why do you care how it feels, just make it run faster.” I think that anyone messing with the field they’re in, and how it’s “supposed to be” gets in trouble and it goes back to that key question: “How much pain can you take standing at the intersection of fields?” I guess I’ve always wanted to feel that pain. I guess I feel alive in it.”

I don’t think we have time to run through the entire course of your career but at a high level, what aspects of your work have you been proudest of, and what about your work activates you?

Wow. Well I think any creative person you talk to will tell you they’re not really proud of what they’ve done, because they’re still searching. So I don’t think I’m proud of anything I’ve ever done. I think that I’m always surprised when I see something I did in the past ­. What I’ve seen about getting older, is you’re like, “Did I do that? I don’t remember doing that. I guess that was kind of okay, but I could have done better” kind of thing [chuckles]. So nothing in particular, really. I’m glad that I’ve continued to learn, try new things. Being in venture capital is my most ambitious art project to date.

I definitely want to go into that with you, in a little bit. In terms of integrating the tech and art worlds, did people see it the way­ or as naturally as you see it? Like, from a political perspective, has there been push­back from either side, when you’ve for instance been pushing tech onto RISD, or pushing art into Silicon Valley?

Yeah. I think. I’m glad you asked that question. I’ve always experienced push­back. In art school, I remember in the early 90s my conservative design teachers told me, “Stop making things move on the screen. That’s not right.” Or being at MIT, and my engineering teachers telling me, “Why do you care how it feels, just make it run faster.” I think that anyone messing with the field they’re in, and how it’s “supposed to be” gets in trouble and it goes back to that key question: “How much pain can you take standing at the intersection of fields?” I guess I’ve always wanted to feel that pain. I guess I feel alive in it.

What are the problems that you seek to solve with your work?

Right now I want to address the fact that most of the power in the world is controlled by people who understand money, and in many cases have understood it for multiple generations.

Creative people are trained to not care for money. I think because of this, creative peope—when I say creative people, I mean like arts, design, or even engineers who love to make things—or “makers” tend to believe that money is evil, bad, corrupting, dangerous. My passion is to enable makers to understand that money is just a medium. And like all media, it can do good, it can do bad. In the same way we can’t say that all art does good—there are bad artists. There are Evil artists. and so money can be used in the same way: for good, for bad.

Similar but slightly different question: What are the biggest motivators in your work? What drives you?

To question what I know, because I’m supposed to know a lot of things. And each time I feel, “Maybe I understand this,” I’m like, “Oh, I don’t get it.” Being in Silicon Valley has been so humbling. To meet people like yourself who are really in a whole different way of thinking that I overlooked, and didn’t fully understand, and I wasn’t a part of. That’s why for me, living here­­ I’ve been living in like a Millennial, I have no possessions, and am living in Airbnbs and Uber­ing everywhere. To understand how your generation feels right now has been an exciting moment for me. I love this project you’re doing and I love how you imagined it and I love how after you have gone through most iterations of yourself, you came to see this as important and there’s nothing to stop you. You just said, “I’m going to do it. Suddenly, I have 500 people who want to be a part of it.” And I thought, “Thank goodness that people like you are saying, ‘Of course I can. Because technology is something I’m not afraid of, but I’m not just technologist. I’m a person of culture, and I’ll combine them together and show them.’”

“Being in venture capital is my most ambitious art project to date.”

Amen and thank you. This is a little bit of a side step, but you’re on the board of Wieden, and I’m curious to hear how you apply your perspectives and methodology to advertising.

Oh. Well, a lot of my passion is going back to the world of money, the world of control. I’d like to be a creative person who is in board roles who can argue for creative. So on Wieden’s board, I channel the guy who can talk money, but can talk creative too. The questions always have to be not about pure profitability, but creative integrity. And the reason why Dan Wieden brought me into his world is that he wanted to make sure that all the discussions come back to, “Are we a creative culture?” So I like those kinds of roles, where creativity matters at the very top. I recognize that such opportunities are precious, and are meant to be made into something, and to be taken to their fullest.

When was the moment when money became important to you as something integral in the design process?

It was in the year 2001. It was the dot­com crash. And some of my colleagues at MIT owned a lot of stocks. And we were at a meeting where they were facepalming and going, “Oh no, oh no,” because they were losing all kinds of money. I had no money, so I didn’t know what they were talking about [chuckles]. And oh my gosh. Shortly thereafter, MIT did some restructuring, and I remember there was a CFO type person who said to me, “John, you’re the creative person, so don’t worry about the money. We’ll figure it out. You just go and be creative.” And he was maybe the third person in my life who had said the same thing to me. And when someone tells you, “Don’t worry your pretty little head, John. It’s going to be okay,” I get worried. I wonder, “What are you hiding from me?” And I realized, I would read newspapers and not understand the financial terms ­­ and the legal terms too. Sure, I could read People Magazine, one of my favorite things. And it’s so vacuous, and easy to read. But I couldn’t read The Wall Street Journal. And so I did my MBA to begin to learn the language of the finance and business world to get to feeling, “Oh that’s what you’re saying. Oh that’s what I didn’t understand.” Here I was, limited to being told that I’ll do the creative part, and you someone else would do the money part. I wondered, “How much am I giving away? How do I take back my integrity?” That’s where this drive all came from.

Interesting. Did you ever expect to be in Silicon Valley Venture Capital?

Never. I actually had never heard of “venture capital” until I got to Silicon Valley. Well, I kind of heard of it; but I didn’t know what it was at all. In full disclosure, I just sort of bumble into things. With the attitude like, “Oh, I’ll try that,. I’ll try that.” I remember feeling, “Venture Capital? What is that?” Two months before I arrived I bought a book on venture capital. I read it, didn’t quite understand it. So since I’ve arrived, it’s just been a lot of learning. I marveled at how a little bit of money can become a large amount of money? I didn’t know it was possible.  I then wondered, “Wait, so what are the letters? What do they mean? Oh, they’re in sequence. Okay, I get it.” All these things that I had no idea about­­ and just to realize it now in my lifetime has felt like a blessing.

I’ve also found that people who find out I work in venture capital will say to me, “Oh, venture capitalists, they’re bad, bad”. I don’t know what they’re talking about. I know a lot of bad people in the academic world – and some good ones. And I can say I know a lot of good venture capitalists – they’re pretty amazing. I love how their goal is to see the impossible happen. And when we think in this start­up, Silicon Valley world, that’s a kind of a mantra—you know, “Make the world a better place” or whatever—I love that the people who have the funds to power these things, a significant percentage of them, do believe the impossible is possible. I think that’s magic.

Tell me more about your first impressions of Silicon Valley.

Well, you know that my first impression was – the lack of  diversity in tech, and how there aren’t enough women, people of color, and it’s not addressed sufficiently. I noticed it from the very beginning. But then I noticed that it was because I myself wasn’t making a conscious effort to change that in my own activities. Maybe in my first few months I met mainly young white men, because they would introduce me to more young white men. And so after a while I realized, “Oh, maybe I’m doing this wrong. It isn’t that the system is doing me wrong; what do I have to do differently?” So I began asking myself if I’m having ten people that I’m seeing, how can I now consciously edit my direction. I found that my conversations and gatherings became so much better than when they were less diverse.

So when people say that diversity is important, I like to say instead, “No, it isn’t important. It’s essential to increase the quality of discourse.” When I was leading RISD, I had the opposite problem because there were ~70% or more women in the student body. So I would always be like, “So where are the men?” So again, we have to recognize the situation we’re in and we have to take action. But I’m by no means perfect with regards to my diversity record, but I do strive to be conscious, aware, and take action on the matter.

“When people say that diversity is important, I like to say instead, ‘No, it isn’t important. It’s essential to increase the quality of discourse.’“

Tell me about how kind of the culmination of your previous work impacts how you’re approaching your work in VC.

Oh, absolutely. I became president of a college in 2008 because I read the “Audacity of Hope,” and I listened to the audio book and it was so inspiring as an American to hear that anyone, any American, no matter what age, race, or creed can make a difference. “Yes, we can.” So, when the headhunting firm, Spencer Stuart, called me up and said, “Hey, you want to be president of a college?” And I said, “I can’t do that.” But yeah, I finished my MBA, but I don’t have any experience, and I was never a dean or a provost or all these special titles along the way. I can’t do that. And in my voice I could hear, “Yes we can. Yes we can!”

And so Obama became president that year—the same year the financial crisis happened. Me too, I was brought in as a person who was going to bring in new ideas, and then shortly after I arrive I’m overseeing the worst layoff in the history of the place. And I’m no longer a person with ideas, and immediately assume the role of the pragmatist and operator working to navigate a financial crisis. And it was kind of like a sock in the gut and in the face. And so I had to become a different person. And I’m grateful because otherwise I wouldn’t have learned how to operate at scale as a leader.  I wouldn’t have had to reform the business model, or really understand the business of a university, and to understand where every dime goes. That was a great outcome, but a hard process along the way. And so I come to Silicon Valley to learn that this knowledge of how to run an organization at scale through difficult times is valuable here, which I find very promising and positive. It isn’t that people here are all about fail fast. It’s, “Can you recover fast?” And I’ know how to recover – it just takes hard, and smart, work.

Let’s go really macro for a second. How do you feel about the state of Silicon Valley Tech in 2016? What excites you, what frustrates you?

I think what excites me is that there’s a kind of awareness that maybe we need to make things for more kinds of people than those who live in Silicon Valley. You can call it diversity, inclusion, all kinds of things ­­ it doesn’t matter. We recognize there’s a strong business case for matters that impact people who live outside this region, and by knowing what they care about, we can  actually have a bigger impact. That excites me: not the technology. There’s a realization occurring here in this region.

What turns me off? ­­ I don’t know. I mean, so many things get me grumpy in general, I guess [laughter] if there were one thing that ticks me off, it is that certain voices still cannot be heard, and I believe that with the fortune and responsibility in the voice that I have, I want to do everything I can to amplify those voices. But more work has to be done.

I saw that you started a newsletter recently, for Asian­ Americans in tech.

You noticed that. I guess that I woke up one weekend realizing that, “Hey, I’m Asian.” It was this weird moment that came to me. I mean, as an Asian American, I try to hide. I try to fit in, and that’s been my whole life. I’ve always fought for everyone’s cause whether it’s African Americans, Latin Americans, LGBTQ, and any group feeling social injustice at unfair scales. Anyone. Because I know what it’s like to feel different, but I realized recently that I don’t do anything for Asian people, and it was just this, “Why don’t I?” It’s because I don’t want to people to pay attention to the fact that I am not like them. I realized what a disservice I was doing. When I saw Tracy Chou, ­she’s amazing – I felt I had to do something.

She’s in my project!

She’s like Legolas. She’s  like Legolas with the arrows in how deeply she is engaged in these matters. She made me think, “Wow, I’ve got to get off my butt and say something.” That’s why I wrote the essay, “Did I grow up and become the yellow hand?” Am I the type­-O hand on the emoji keyboard that doesn’t stand for any particular skin color or culture? I felt that maybe I should stand for something. That’s why that began. Thanks for noticing that.

I keep an eye on things [chuckles]. I’m on Twitter a lot when I’m not shooting. Let’s see, I’m curious to know your thoughts on how Silicon Valley seems to approach design.

Oh, it’s very exciting. What’s so exciting about how Silicon Valley works is that it lives in the true era that no one could have imagined, where the product is no longer five zones removed from the consumer. There is no need for the intermediary to sell the water bottle that you drink; it’s right there on the other side of the phone’s glass. You’re using the product, and not only that but it’s being used not by a few people but millions of people. So Silicon Valley designers deal with a significantly different kind of design, the design where the product is the brand, is the expression, is delivered in real time, and it can be changed every day if the budget existed. Whereas the old design is, “I’ll make these glasses, I hope they’re awesome. We shipped them; they didn’t sell. Well that’s because I was a genius and people didn’t get it.” Or, “I shipped my glasses and some sold. Hmm, okay well let’s get lucky next time.” Silicon Valley designers live in a world where the thing they’re selling is never going to be done being made, and is being shipped live. That is an amazing thing, and these design outcomes are fundamentally different than how design was done in the past. And the designers suffer at the same time too, because people who made things like in the old world got to finish it. “It’s done. It’s been finalized. It will never change now that it’s done. Isn’t it amazing? It so amazing. It’s done.” Whereas people who design in tech never get to be done. So when I saw that you were a photographer and you were taking photographs, you were able to go back to the world of “done,” because done is the best place to be. But you have both in you. You know exactly what that’s like, you know what this it is like for designers in tech. And you’re still so young, so you’ll find all these new things in your life. It’s being in this imbalanced place, that makes you a unique person in the future, I believe. That new person is part of your project. I think you’ve just started.

Thank you.

You’re like, “Oh, this is something. What is this?” Scratch head, scratch head. This is a good beginning.

This is the kind of work I’ve been wanting to do my whole life, and this is the first month that I feel like I’ve had the time and the resources to do it.

That’s good. You’ve earned it.

I do feel like I’m just at the beginning. So I appreciate the encouragement.

Absolutely.

What are your thoughts on the relationship between tech and art here?

It’s tough. In New York, it’s easy to be an artist, because there’s a lot of artists there. There’s a history of art galleries there. For example, if you’re in Paris, it’s easy to be an artist – it’s also easy to be a mathematician, I hear. Here the spirit of art is not a strong spirit, which I think signals great opportunity. And I think people, like yourself, who can seize the moment and think, “Well, maybe there isn’t a strong art community of a certain art, but maybe there’s a strong community for a different kind of art.” I think that work will be done, and that work has to be done.

Even the fact that you’re reaching out to the world and pulling people into this world that you have ­­ that’s a different kind of art. It’s like Jenny Holzer taking portraits, 80 portraits, live around the world. That feels like a kind of art that’s natural here and can be celebrated, versus old school, like “Let’s take a motor and let’s attach it to a paint can and let’s make art.” And hearing a gallery crowd cheer you on and say, “Oh, my gosh. That was amazing art. It’s right in front of me. It’s finished. It’s done.” That’s not art anymore – at least for people in the future. The new art lives with people. And I think this region would be more likely to understand that. So I’m hoping that the gallery system can evolve to accept that future. I’m sure it’s going to happen, but it’s going to be a problem for a while. If you have more of that kind of art, then the new kind of galleries will emerge, and the market will emerge from that. And I hope that you, Helena, will sell different aspects of your process as products to find that different audience and to help this region talk about art in the new language your generation will create.

One thing I’ve noticed interviewing designers, particularly designers who have worked on the East Coast and in New York city, is the frustration at a lack of philosophy in start­up design. In my experience, I remember at least, when I worked in Tech, how much technical specialization is valued versus philosophy, and I’m curious to see I you have felt any of that yourself.

Yeah. This may be a kind of blasphemy, but I used to be a member of those cults of the old world’s philosophy. I was long a part of the Swiss Typography mafia in Shinjuku. At the time, I loved the perfect movements of type by 0.001 points – where the average human being couldn’t really tell anything had changed. Invisible details, you know? I used to love that. And then I realized it was a cult, and a form of brainwashing. It was a constraining thing. It was a safe place to be, and great to have learned.

So both skills are important – the place of safety that the past provides, and the new things that can be made in the medium of technology. It’s the people who can go across the two, fluidly, that I think this region needs more of. But if you take a viewpoint of, “I know philosophy; you don’t. So you suck.” Or, “I can code; you don’t. So you suck.”

“If there were one thing that ticks me off, it is that certain voices still cannot be heard, and I believe that with the fortune and responsibility in the voice that I have, I want to do everything I can to amplify those voices. But more work has to be done.”

It’s almost like both sides are the same in that way, which is funny to think about.

That’s how sides are made. There are those who say, “I know this; you don’t know that.” Then another person nods in disbelief, “What? You don’t know that? Really? You didn’t know that?” Hmm. I’m so over that kind of thinking. I’m not into that at all. We can all learn from each other.

What are your photographs behind you? What are they?

Some are mine, some are from friends. I try not to have my own photos up there, because it feels like I’m looking at my own iMac screensaver or something.

I understand.

Or having like a portrait of yourself in your bedroom.

It’s a bit awkward, I understand.

Okay, where do I want to go now? What are you working on right now, in 2016, either for work or for yourself?

I’m working on the 2016 #DesignInTech Report ­ ­the second edition. Last year it came out at SXSW. I thought it would get 50,000 views—it had 850,000 views. So, surprise! Sheer luck. I’m like, “Woah.” I’m making the new version—that’s coming out in three weeks, so I’m sitting in front of Keynote, moving things around, and tossing things out. I hope it’s able to communicate this relationship between business, design, and tech that I care about.  I want to keep showing how it’s valuable, and that you can assign dollar signs to it: DESIGN is DE$IGN. Some people consider the dollar signs as being dirty, or just outright wrong. But I consider it work that I get to do right now. So I’m going to do it.

How is life without possessions right now? Do you feel like you’re going to stick to that for a while?

It’s been really great. I was observing how younger people live lighter lives, so I’ve been getting to live that right now. When I was at RISD, I had an 18 room mansion with six bathrooms or whatever, and I didn’t have that much stuff anyways. Now I just kind of have a suitcase and travel light, and after I broke my right arm over the winter holidays by tripping while on a run, I can’t carry as much now. So I’m even lighter now.

That’s interesting because I’ve historically been a person who gets rid of everything she owns every time she moves­­.

Interesting.

And I’ve moved a lot. And this is the first time I’ve ever put things on the wall in my apartment. It’s the first time I’ve ever had more than a Craigslist couch or a Craigslist bed. It’s really new and interesting for me and I think it’s been good for me in a way because I think I would have moved from San Francisco for reasons that don’t even make sense, like, “Things are great. Let me just completely like throw it all at the air and move somewhere else. But this have forced me to be stable for the first time in my life. So I think it might be good for me for now.

That’s the thing; you live different lives. So this part of your life is this.

Where do you see yourself in five or ten years?

Wow. I hope that I’m still involved in the start­up world. I hope I’m making a start­up, or I hope I’m at a start­up. I’ve just learned so much from the start­up generation. I figure I have to learn more by being in that world. That’s what I hope.

My last question for you would be, based on the lessons you’ve learned through your own experience or the experience of those you’ve taught, what advice would you give to young designers just getting their start in tech?

I would strongly suggest that they be curious about business because business is only scary when it’s not understood. People who are creative especially in the tech world will be looked down upon unless they are curious about business. Everyone’s got a different language. The more languages you speak, the more positive damage you can do on the world [chuckles]. So that’s my take.

“I would strongly suggest that they be curious about business because business is only scary when it’s not understood. People who are creative especially in the tech world will be looked down upon unless they are curious about business. Everyone’s got a different language. The more languages you speak, the more positive damage you can do on the world.”

I was born in Brooklyn, New York to a pretty warm family. They’re predominately blue collar on both sides. My dad was born in Nigeria and lived in Sweden. My mom was born in Trinidad, an island seven miles north of Venezuela. She moved to the States when she was a teenager to continue her education. After college, she settled in Brooklyn, New York where a lot of her family lived. My father-to-be was still a continent away in Scandinavia.

My mom had a good friend who, just like her, loved to travel the world. This friend was doing her master’s in Sweden and invited my mom to visit. On her trip over, she caught a cold but mustered the strength to still go out and do things. Then one day she went to a local church and found herself sneezing a lot. A gentleman sitting behind her kept saying “bless you.” Later that day, the church had choir practice. My mom, an amazing singer, ended up practicing with them. Further into practice, she started singing a song that the “bless you” man started playing the piano along to. She turned around to who would become my dad. Obviously he got her number.

They started dating and, after some time, got married in Sweden. This was 1993. I was born September 14th the following year in Brooklyn, New York. But my dad, in need of a sponsor, wasn’t able to make it to the US in time for my birth. He was distraught. I was cool with it because I was five minutes old. My dad was still finishing up his Master’s/MD program, so the distance from his family definitely affected him. He was finally able to move to the US in 1998. In the four-year period before this, I briefly lived in Trinidad to learn about culture and be near my mother’s family. Then we lived in Sweden to be with my father. “We” was my mom, myself, and my half-brother. We have the same mother and different fathers, but my father was definitely a father to him too. I’m close to my brother. We’re 12 years apart, so growing up wasn’t your typical sibling-relationship, but it worked and still works for us.

“Maybe that’s why computers were so interesting to me. A way to “escape” into a new world, full of possibilities. Where the cure to loneliness was a Cmd+T away.”

Growing up in New York, I was surrounded by South Caribbean culture. Most of my father’s family lived in Maryland, so although I knew and occasionally visited them, I didn’t know their culture too much. However, when it was time for my brother to go to college, my father suggested we move to Baltimore, Maryland. We did, and all of a sudden I was surrounded by African culture. Stark difference.

Baltimore was a major change from Brooklyn. New York is fast-paced. Maryland is not. New York is dense. Maryland isn’t sparse, but it’s not New York level either. And we lived in Baltimore County, not the city. So it was even more laid back than my previous home. People drove more and rode the bus less. The transportation system was complete crap. I got used to all of it though. I also got used to my dad’s family’s culture. My mother has two siblings. My father has six. Four of whom also lived in Baltimore at the time. His family is very close, so I’d see my cousins more than some people saw their siblings. They all felt like brothers and sisters to me, but then I’d have to go home to no kids whereas they had their own siblings. Looking back now, I realize that I often felt alone as a child, yearning for my brother. I’d see him like twice a year when he was doing his Bachelor’s and Master’s, but I got used to it. Maybe that’s why computers were so interesting to me. A way to “escape” into a new world, full of possibilities. Where the cure to loneliness was a Cmd+T away. Still, my family’s culture taught me the value of family. I finished up elementary school in Baltimore, then attended middle and high school. Childhood was fine though. No sleepovers, culture thing. First job was cleaning our church. Oh, and I got a ton of migraines. They’re gone now. Thank God.

I remember in elementary and middle school, I used to talk a lot. I also asked “too many” questions. My parents said it was because I didn’t have a sibling around to play with, so I’d get bored. When I’d finally see another child, it was like a seeing a new species and I’d feel the sudden urge to tell them all the things. Of course this was much to the dismay of teachers, so I’d often find myself in trouble. However, one of my teachers in elementary school didn’t see my talkative nature as being a “disruptive child.” She saw boredom and sought to challenge me. She put me in a program called GT, or Gifted and Talented. It was a track for students who should probably be a grade or two above, but didn’t skip. One year into it, I was still talkative, but it was much more bearable. I also felt challenged. Looking back, I really appreciate what she did for me. Most of my teachers told my parents that I had a learning disability, or that I exhibited traits that often lead to dysfunctional people in society. This teacher just saw me for who I was. A bored child. Thanks, Ms. Gaston.

This was probably the first identification that maybe my skills and interests were not aligned with those of my classmates. I was the “draws all over his homework” kid. Of course, I learned to conform. Just like I had to conform to desks designed for right-handers when I was part of the left-handed club. Then in middle school, my attraction to web went through the roof when I stumbled upon code. I found it so intriguing to be able to do whatever you want and put up whatever you want with no teachers around to strike you seven points. It was ultimate freedom and I wanted it. So I taught myself HTML and CSS, then starting hacking around.

I started doing websites for family, then family friends, and finally strangers. I remember setting up a Paypal account to collect payments. I connected it to my checking account that my mom let me sign up for. It was a branch of Wachovia built for children. I remember taking on some projects that required Flash or some heavy JS. Instead of turning those projects down, I’d say “oh, I can do that!” Then I’ll read up tutorials or would find things around the web I could build off of, like Wix. Ugh, I used to use Wix. I would figure out what the yearly cost was for services like Wix, then would add on a premium to the project total so that I’d collect a profit at the end. It was cool getting those monthly or yearly charges from services I would use for the projects. Sometimes I’d mis-plan and go in the negative, but I was learning. Design and business. After two years of this grind, I was able to save up for my first Macbook. Third-hand off eBay.

Daytime, I was in school. I started identifying the classes that interested me the most. Math, psychology, and English. Math had systems and frameworks. Psychology broke down the way people think. English, had creative writing – freedom of expression. I found it very interesting because it was the one type of assignment where your teacher could only grade you on grammar and spelling. There was no such thing as a bad idea. These things stuck with me, and ultimately influenced my design career.

English class ended up leading to another passion – blogging. I started my first blog over a school summer. It was called mediainfive.com. The goal was to capture the top news of the day and synthesize them into a five minute digest. The site probably got 100 views per month. I’m pretty sure they were my mom and her friends showing me support. I ended up pausing the blog when I returned to school. My second blog was called trendingweb.com. It consisted of interviews I’d conduct with entrepreneurs from around the web who were building cool stuff. Their products often had little-to-no users at the time. Some of these companies turned out to be Zerply and 6Wunderkinder, makers of the todo list app, Wunderlist. These blogs also led to writing opportunities at bigger sites. I did an internship at AppAdvice, a blog that focused on Apple’s iOS store. At the time, it averaged a million views per month, so that was a big change for me.

Writing 5–8 articles a day for them taught me discipline and polish. A lot of the practices I learned there would stick with me down-the-line. Afterwards, I wrote for a blog called Macgasm, also focused on Apple. This site was incredible. It was the first time I “hit” Hacker News, Google News, and broke a site from web traffic. It also led to me visiting San Jose to attend a tech conference, where I got to meet really inspiring people who would become friends in the future. Chris Anderson, the founder of TED, and Mark Johnson, then CEO of Zite, were a couple of them. On my way back from that trip, I remember reaching out to Mark for an interview. I wanted to play around with a new format of recording an interview, transcribing it, then summarizing it into a sort of story with pull-quotes. If you saw my recording setup, you’d laugh. But it was different, and he was down for it. It spawned a series of interviews of a similar fashion that I did for Macgasm, and led to me getting my own column. I met other friends through this column like the Sparrow, Flud, and Instacast founders. Looking back, it was an evolution of TrendingWeb. I’m grateful for having had that experience. And I’m grateful to my parents for letting me pretend to be sick, so I could skip school for a few days for the San Jose trip.

By now I was in high school. I attended Overlea High. It was a big change from my middle school. Parkville Middle was in the top 10 in Maryland. Overlea High was in the bottom 10. Why did I go there? In our school system, each student had zone schools, or schools they’d attend by default based off location. Golden Ring Middle and Overlea High were my zone schools. After elementary school, I applied to Parkville for their magnet program. In it, I got to take interesting courses like Mass Communication, Visual Arts, Environmental Sciences, and Applied Engineering. When high school time came around, I applied and didn’t get into my school of choice, Eastern Technical High. The number one in the state and top 5% in the country. In the future, I learned that some parts of my application were mixed up with another student, costing my acceptance. No one thought to correct it and I ended up at Overlea. Most of my friends went to Eastern, so day one of Overlea was definitely an adjustment. It was pretty bad. First day, there were at least five fights and three suspensions. We even had metal detectors at the school’s front entrance.

“I remember students joking during my first few months that I probably got into numerous fights, or that I was a thug, etc. The theme was that I was lucky for even getting into Eastern, and that I wasn’t going to succeed at the school. I mean, during week one people would literally move out of my way in the hallways.”

But I found the good. Our school had a program called DECA – Distributive Education Clubs of America. It’s very similar to FBLA – Future Business Leaders of America. It was a business club for high school students that had competitions at the county, state, national, and international level. My club-mates and I competed our way to internationals which took place in California. We traveled for the contest, and although we didn’t place at that level, it was an amazing experience. It was a big deal for our school. It was also my first dose of California weather. I knew I’d be back one day.

Halfway through my first year of high school, Eastern Tech announced that they would do something they had never done before – allow students to apply to enroll in 10th grade. My parents were all over this. I applied and got accepted. I later learned that only two students were accepted state-wide. My mom was excited, but I didn’t care anymore. I had gotten used to Overlea, built some friendships, was top of my class, and didn’t mind the fights anymore. My mom wasn’t having it and, come the following August, I was an Eastern Tech student.

Tenth grade. I remember showing up to school on day one. People looked at my funny. Was it because I came from Overlea? Was it because I didn’t look like anyone there? Maybe both. I was coming from a school that had a very negative stereotype. I was entering a school that was probably 75% Caucasian and 2% African-American. I remember students joking during my first few months that I probably got into numerous fights, or that I was a thug, etc. The theme was that I was lucky for even getting into Eastern, and that I wasn’t going to succeed at the school. I mean, during week one people would literally move out of my way in the hallways. Like, did they think I’d shove them or something?

It took about half a year for me to settle in and for the negative sentiment to “settle down.” Like Parkville, Eastern provided magnet courses that students could major in. The options were Health, Automotive Technology, Business Management and Finance, Interactive Media Production, Construction, Culinary, Engineering, IT, Law, and Teaching. I chose IT, the closest I could find to my evening passion of coding. I later learned there was little overlap, but I still learned a lot. By graduation, I was CCNA-certified and could work entry-level for Cisco or the NSA. I didn’t do anything with that certification, but the knowledge was valuable. I remember learning how to make ethernet cables from scratch, and at least retained the knowledge for fixing my wifi when it acts up. However, I realized in 11th grade that although it was interesting, IT was too technical for me. I didn’t want to fix the Internet, I wanted to build awesome things on it.

“Online, I experienced more ageism than racism, primarily because I hid my face for a long time.”

This realization led to me noticing that my true passion lied with websites. How they looked and how they worked. Up until then, I had messed around in Photoshop and tried to design, but I didn’t consider it a skill. So I decided to change that. I started reading blogs like A List Apart and Think Vitamin. Then I’d find designs from around the web that I liked and would try to reverse engineer them in Photoshop. I did 2–3 a night. It didn’t take long for the practices to commit to memory. However, I couldn’t find much content on what it meant to a designer. Or a content that covered the developments of the design industry. Like, what tools were people using nowadays? Or what we could learn from the most recent hot app? I don’t know why I felt like I was the one to do it, but I told myself I’d create a blog for this. I met my blog co-founder, Drew Wilson, on Twitter. A couple months later we started The Industry.

This was November 2011. Our tagline was “covering design-focused startups and people.” In our first month, we had a couple thousand visits. 6 months in, we were averaging one hundred thousand. Drew handled the design, development, and promotion. I handled editorial, and sponsorships. We ended up building an editorial team of 12 people. Our first, and most loyal sponsor, was Squarespace. We started a podcast with Adam Stacoviak, and within months, it had surpassed the blog in popularity. It also represented a majority of our revenue, which I used to pay our editorial team. The team was distributed. None of us met in person until years later, but it was a true passion project. I remember writing, editing, and coordinating with the team in the evenings and weekends, then reviewing articles to publish at school during lunch time. The team is all in great places now. One’s a designer at Microsoft by way of Sunrise, another is just crushing it in New York, another is a writer at Invision, one’s VP of Design at Acorns, etc.

I didn’t know it at the time, but the podcast which we called The Industry Radio Show, would play a huge role for me. Each week, we’d have guests on to chat about design. I’d notice patterns in their background stories, what they did day-to-day, and what they were most passionate about. They were describing my job description. A lightbulb went off in my head. I told myself, “okay, this is the kind of work I want to do. The best of all worlds. Write, design, code.”

“My dad’s an optimist, but it hit him in that moment. Because he knew that something as small as someone just slightly discriminating against you could destroy your life. For him, it was something that could have kept him from his family indefinitely. For me, it was something that could have ended my chance of going to college and put in jail.”

High school was wrapping up soon. I applied to one university in Maryland, and two in Pennsylvania. UMBC, Drexel, and UPenn. I got into them and was now faced with a decision, but I couldn’t shake the feeling that I didn’t need any of them to pursue my newfound job description. I had become jaded to the whole college thing, but didn’t throw it out altogether. I knew it was important to my family, and that I would be judged by my peers if I didn’t go. After all, there was a stereotype. I opted for Drexel with a major in something design-y, and a minor in psychology.

That was the plan. Graduation came. I remember sitting down with my class and facing all the parents, thinking to myself “I wonder how many of them are doing what they love as a career?” Then I looked around to members of my class. Some had huge smiles on their faces, knowing that they got into the school of their choice, their boyfriend was coming with them, and that “everything was going to be awesome.” Some had partial smiles on their face, knowing that they were going to get the education they wanted, but at the cost of their parents savings or theirs. Some, like me, were expressionless. Were we all thinking the same thing? Were we all thinking “is the future really as simple as getting a degree and getting a job? Or must we find our own path?” I don’t know, but I know that’s what I was thinking. In that moment, while our valedictorian spoke, I decided to choose my own path. Step one was finding an alternative to college.

I started thinking about the guests from the podcast again. How did they find their path? I also started weighing the education system against this “choose your own path” model. It leaned heavily to “choose path.” I recalled the feels I’d get when I’d ship a website for someone, or publish an article on the blog. Or the fact that Drew, although years older than me, didn’t care about my age or race. He just appreciated my work. I then thought about school, and some of my teachers dating back to elementary school. My quarrels with how tests were set up for memorization and not comprehension. The racism and stereotype I felt coming from Overlea. And finally, how I nearly lost it all by an ungrounded accusation.

“I know that’s what I was thinking. In that moment, while our valedictorian spoke, I decided to choose my own path. Step one was finding an alternative to college.”

About that accusation. About 1–2 months before graduation, I woke up late for school. The night before was a long one for The Industry. My dad drove me to school. I exited the car, walked into the front office, signed the late slip, then proceeded to my homeroom. In my second class of the day, the assistant principal and another faculty member came into my class and stopped it. They asked me to come to the front office with them. The tone was anger. I was completely puzzled and remember hearing mumbles from students that I was probably in big trouble. But for what? We finally got to the assistant principal’s office and the other faculty member said in a demoralizing and assertive voice, “We were informed this morning that you have been dealing marijuana around school and that you came in this morning smelling like it.” I was shocked. I asked where they got that information from and they said they couldn’t reveal that information. I then told them to check their cameras outside and at the front-desk. “My dad drove me to school. You have a camera outside looking at everyone who walks in. If you check that camera and check the timestamp, you’ll realize that 15 seconds later I was in the front office, which also has a camera. You’ll see that I signed in and left for my homeroom. You can then talk to my substitute homeroom teacher and ask when I got in. And then you’ll know that there was no way I could possibly have done anything in between that time.”

As I was saying this, it hit me who made the accusation. My substitute homeroom teacher. When you get to school late, they’re the first person you go to before heading to your class. That day, I went from my homeroom teacher to the class I was pulled out from. It had to be her, so I asked. They froze. Without speaking, they had answered. At this point I was just trying to keep my cool. I started smelling myself out of curiosity. I wasn’t sweating or anything, and I showered that morning. I smelled normal. So I asked them to smell me. One of them asked, “what?” “Well you said that a teacher said I smelled like weed. You just pulled me out of a class. I’ve only been in school for 30 minutes. I haven’t changed my clothes. Smell me and tell me if I smell like weed.” The assistant principal did. So they leaned in and said, “Yeah, I don’t smell anything.” By this point, logic had won. I had also proven a point. Before doing the simple act of following up with the teacher, or checking the cameras, they were convinced. That was wrong. Not to mention, they threatened that I could lose my college acceptances, scholarships, and that I could be arrested right then and there by the police officer standing outside.

Even though logic had won, there was something painful in the back of my mind that I learned growing up. By being black, I was at a disadvantage by default. So when faced with such situations, I had to keep my composure and let nothing else show but my logic and reasoning. Somehow it worked. The faculty guy said I could go back to class and that they’ll talk to whomever to get to the bottom of the situation. I nodded, but before getting up I noticed something outside the front office. It was a wall of the names of students who got higher than a 2,000 on the SAT. For the mic drop, I turned and said “by the way, I notice that my name is missing from that wall. So after you get to the bottom of this, do you think I can be added?” Then left. The rest of that day was draining. I couldn’t think, eat, or talk. I went home looking like a zombie. It didn’t really hit me until I got home. I started breaking down. Why the hell was this happening to me? And so close to graduation? Could I really have lost everything in that moment? What would have happened it I didn’t react the way I did? I was afraid to tell my parents, but finally mustered it right before going to bed. They were in pain after hearing it. It reminded my parents of something that happened to my dad in Sweden that nearly put him away for a long time. Something he didn’t do, but was accused of doing because he “looked like someone who would do it.” Sad part? The thing he was accused never even occurred. By anyone. Now his son was experiencing something similar.

Holy shit.

My dad’s an optimist, but it hit him in that moment. Because he knew that something as small as someone just discriminating against you could destroy your life. For him, it was something that could have kept him from his family indefinitely. For me, it was something that could have ended my chance of going to college and put in jail.

Wow.

Needless to say, that dampened things for me. After he was told, my brother took a train from DC to Baltimore with the intention of going into my school. I wasn’t looking forward to it. I didn’t want to be “that kid.” The one who doesn’t let things die, but drags them out after a resolution had been reached. But my brother made a valid point. “It’s not a matter of settling things. They need to understand; one, what they did; two, why it’s wrong; and three, to never do it again to any student, right.” I felt confident that he’d handle the situation well. If you think I’m articulate, just meet my brother. He doesn’t lose. He didn’t. I don’t know what he said to them, but the same teachers who pulled me out of class showed up to every one of my classes that day to deliver the same message. As if from a script, “Hi. We just want to come by and let all of you know that yesterday we pulled Jared out of the classroom because he was suspected of an act. We know some rumors have spread around the class. Rumors are detrimental to students. They can hurt your reputation. We want to clarify that Jared did not do anything. He’s fine. He has not done anything wrong. We will not tolerate rumor and gossip.” I felt so warm inside. My family had my back. My brother had my front. Being his younger sibling, he felt the need to protect me at all costs. Especially from something he knew was real and out there. Obviously, students still gossiped, and to some I remained “guilty” through to graduation.

So that evening, the evening after graduation, I pondered on the podcast. I knew what I wanted. I remembered an episode with a designer who was also an advisor to a company called Treehouse. I loved Treehouse. I remembered Carsonified, the company it came out from. I use to read a blog they published called Think Vitamin. I was intrigued by Treehouse’s mission, so I reached out to its founder, Ryan Carson. I told him what got me excited every morning, what got me excited about Treehouse, and how I felt I could contribute. After a series of interviews, I got the job! I came on as editor of Treehouse Blog, a spinoff of Think Vitamin. It was a dream come true. To help shape the presence of a blog that came from something that inspired me just a couple years prior. Of course I still did The Industry nights and weekends, but we discussed and agreed on a way that the sites would not compete with each other. Our tone, content, and audiences were different.

My job involved helping on building an architecture for what would become their blog, newsletter, and marketing. It was my first time working with product designers. They were my favorite. A month or so into the job, the remote Treehouse employees were flown into Orlando for our team get-together. It was an amazing feeling seeing other people who were all part of the team, building towards the same vision. However, by the end of it reality started settling in that maybe I might still have to go to college. Although I wasn’t the most passionate about it, my parents still expected it. I remember having a conversation with Ryan telling him the possibility. At first, he was caught of guard. And of course he was. After all, part of the mission of Treehouse was to provide the education I was passionate about, so that people of all ages didn’t have to spend tens of thousands acquiring the skills. Especially if the curriculums had a high chance of being out of date. But he understood where I was coming from. Ultimately I left Treehouse after about four months, but it was an incredible summer full of lessons and confidence boosters that I wouldn’t be aware of until months later.

I met up with two guys on the Internet. Both were from Kansas, but none of us had ever met in person. We all shared a passion for emails. I became fascinated by it when I interviewed the Sparrow founders a year earlier for the Macgasm column. We also shared a passion for the potential use of iPads in the workplace. We were like, “let’s start a company.” We called it Evomail. Evolved email. In hindsight, bad name. Sounds like evil mail. We really had to enunciate the “vo” or people would look at us awkwardly. I’d like to say that we were on to something. Some of the things we built are now in products like Inbox, Outlook, and other apps. Didn’t come directly from us, but patterns make their way around eventually. Some of the things I’ve yet to see in a product. One of the things we wanted to do, was to recognize if an email came from a person, or a service. If it came from a service, was it informative or a subscription? If it was informative, could we treat it like a notification? Imagine if you got an email from UPS, that should not take up the same cognitive space as an email from a close friend.

Evomail was going well. We knew what we wanted to build and we were building it. It was an amazing experience cutting new builds everyday, and putting them in my parents hands. Although they didn’t exactly know what was going on, the builds were enough to show them that I had found my passion. Communication. Communication by words, process, and pixels. It also bought me some time off of college. I negotiated my parents into letting me take my first year off of college to work on Evomail and The Industry. On my 18th birthday, I decided to write a blog post on the blog. The target was other creatives in my age group. Those who had a burning flame of passion inside them that they were constantly afraid would be blown out. Blown out for age, race, gender, and what have you. I wanted to address the age piece, so I spent my entire birthday drafting a 6,000 word biography of my journey to finding my passion. With an undertone of “keep at it, friend.” Somehow it blew up! I woke up to it being #2 on Hacker News and the most read article on our blog! I started getting comments from others saying “I’m 17 and I love blank!” “I’m 19 and I do blank!” It was an age-coming out party, and everyone was loving it, or so I thought.

Although he never said it directly, I sensed a perspective change from one of my co-founders. It’s as if I went from being an equal to being an intern. It was ironic. I “revealed” my age for the first time because I was finally confident. And apparently lots of people were hiding it for the same reason. But who knew that my decision would hurt me in my own company?

The following January, Mailbox announced their app with an awesome product video. In one of their initial press articles, a reviewer mentioned that a big problem for the app might be their lack of labels. I felt otherwise. So I wrote an article on my blog expressing that although they were competition, I felt that they were approaching the inbox from an interesting perspective. And that I looked forward to the hustle. Without intention, the article made its way around and ended up as something Mailbox would reference on Twitter when asked by people why they didn’t support typical labels. Felt like good karma. The CEO then reached out a few weeks or so later. He mentioned the article and Evomail, having seen some of the design on Dribbble. Although nothing was said directly, he seemed interested in what we were building. Especially why we started with the iPad. I remember telling my co-founders this–expecting a positive response. Instead, the CEO reacted a bit displeased. As if I had done something wrong by it being me who interacted with Mailbox and not him. A month or so later, Mailbox was acquired by Dropbox.

“Although he never said it directly, I sensed a perspective change from one of my co-founders. It’s as if I went from being an equal to being an intern. It was ironic. I “revealed” my age for the first time because I was finally confident. And apparently lots of people were hiding it for the same reason. But who knew that my decision would hurt me in my own company?”

Around this time, I learned about a program in San Francisco called Bridge. It was a 3-month program targeted at Product Designers who wanted a dose of Silicon Valley. I was intrigued. After weeks of negotiation, I convinced my parents. The deal was “3 months in California, then you come back to start college.” Come April 2013, I moved out to San Francisco. By this point, the collaboration at Evomail had significantly broken down. We were all working hard, but not as a team. I still felt the same vibes from the “birthday article,” and other events occurred that just amplified the feels. Around three weeks into San Francisco, I got a phone call. It was my co-founder. We talked about ways for me to push the Evomail brand now that I was in San Francisco, but then the conversation started to changing to “so what if you move into more of an ambassador role?” Of course this seemed completely weird to me. Every founder is an ambassador of his or her product. We agreed that there was no need for a “role change.” A month later, I got another call. I was getting kicked out of my own company. My stake was depleted, and I was left with nothing. The product launched a few weeks later with mixed-to-positive tech press. I received no credit for my work, but I didn’t care. What pained me the most was that the product I had invested the last 10 months of my life into, deferred college for, didn’t take a paying job for, was gone. Just like that. I felt like I had lost a child. I felt so sick for the next three months. I won’t go into details, but trust me. It was not fair, it was cold, and it came back to bite the company. I learned so much from Evomail. It was the first digital product I designed from scratch. It was my first startup. It was my first termination. It was my first sense of purpose. It was my biggest sense of defeat. God, it hurt, but looking back I loved that I went through all of that. Of course, that’s how I felt in the moment. It made me feel my age and race again. How many other people would do this to me in the future? I started dressing older, forcing myself to talk deeper, and prioritizing phone calls over in-person meets.

A few weeks later, I got a call from a big tech company, public, voicing interest in Evomail. This company would have made me a millionaire… before taxes [laughs]. Although I told them that I was no longer financially invested in the company, they pushed for a conversation. They were kind of like, we still actually want this thing, so we can either hire you for our mail team, or you can reach out to your ex-founders and push for a deal… getting your stock back in the deal. I remember having to deal with that. I sought advice from close friends and my parents. The feedback I heard was either, “I don’t know what to do. It sucks to be in that position.” Or, “don’t take it.” I didn’t take it. I told the person I was in contact with that I would be passing altogether. And that if they still wanted the product, to reach out to the remaining team. I didn’t tell the team because communication had ended between us. However, I did end up making peace with the other founder, not the CEO, a year later when he visited San Francisco. I never really had issues with him. He was just too on the fence. There are certain things you’re just not on the fence about. I feel like he – and he kind of admitted this a little – just didn’t speak up. Apparently, after I was kicked out, a few months later, the CEO tried to remove him too.

“I started dressing older, forcing myself to talk deeper, and prioritizing phone calls over in-person meets.”

But the “fear your age and race” thing started to creep back up again. Was this graduation all over again? Thankfully, I didn’t experience it much at my first job in the city, Omada Health. I was hired as their first full-time product designer. I remember having a good experience there, but I did feel treated like a child at times. Especially by co-workers who had children. Some with children around my age. To some of them, I could be their child, which is true. But, I’m not. I’m your co-worker at a company that we both work for. Don’t treat me like I’m your child. People asked why I left after six months. Part of it was that I worked on an interesting project, finished it, and felt good about it.

I was only really supposed to be there for three months anyway. My parents wanted me back for college. I stayed on longer because the project was fascinating. Building a product that allowed pre-Type II Diabetic people take back control of their health. My project was over, and I felt like I had gotten a good dose of the medical field. Most of my father’s family is in it, so my tolerance was only so high [laughter]. But part of it was that I didn’t like feeling like a child amongst adults. It wasn’t that I wanted to be treated like a boss. I just wanted to do good work and be respected by my peers. I felt like I was doing one, but only getting half of the other. I still appreciated my time there and the people I had an opportunity of working with. They gave me a beautiful send off. I left the day before my 19th birthday.

My plan was to take a break, but that lasted all of one week. I joined Obvious Corp, the organization behind Branch, Medium, and Lift. Lift, the habit tracking app. I worked on that. It was great. I worked on the 2.0. I was only there for less than a year though. My parents, coming from a different generation, felt that four jobs in two years seemed weird. They wanted to know if I had a plan, or if I should just move back east and go to school. “I promise you. I’m not fickle. I have a vision, and I’m making mistakes along the way. But these mistakes are lessons and I’ll figure it out in the end. I learned, four times.” I told them that my plan was to contract, build work and social credibility, and when I’m ready, to find a role where I will be respected and do good work. They agreed.

I did some contracts. One was Nuzzel, a news app. Another was Bloomthat, an on-demand flowers product. I did some other niche products too. It was really fun! I got to work on Bulan Project, something by my friend Elle Luna, with other friends of mine. Those were creatively liberating and fun. Then a really close friend of mine reached out and was like, “Hey man, if I told you there was a company that I would join, would you join?” And I’m like, “Yeah, if such a company existed.” Background on this dude. He does not full time. Period. So I asked him why he wasn’t there already. “Well, I just finished YC, I have a company, I’m about to have a child, and we’re thinking of moving to Hawaii.” Fair. So I said intro away. He introduced me to a company called Teespring. I met their co-founder, Walker. Within minutes of talking to him, I knew he hired talent and only talent. He didn’t care who you were, what your background was, your race, age, or gender. He just cared if you could do good, passionate work. I never left a meeting so passionate about a company or so trusting of its leadership. I joined a month later as Creative Director. 

The first thing I did was redesign the logo. Second was build the team to five product designers and one brand designer. By the end of 2014, I was designing and managing a team at the same time. I had to learn fast. With time I found myself less and less in Photoshop or Sketch, but in meetings working to figure out the direction of a business that, between joining and leaving, had 20x. The growth was fun to watch. We went from 30 people to 300+. But with the growth of the team and product, I had to juggle managing a team and still designing. It wasn’t easy, but I developed invaluable muscles from the grind. The lessons were numerous. From what it means to grow a team, to growing yourself, which is just as important. If not more. My time at Teespring was similar to Omada Health. Great product, culture, and growth. But people are people, and everywhere you go, you’ll meet some who are partially blinded by attributes that don’t pertain to your output. After a year and a half, I left to take a break and detox from the grind. I intentionally didn’t have a plan.

“But people are people, and everywhere you go, you’ll meet some who are partially blinded by attributes that don’t pertain to your output.”

I took about two weeks to do nothing. I read, called my parents more, caught up on some shows, and took more walks. Greylock and Fuel Capital became my home. I started working out of one, and contracting for the other’s portfolio companies. It was fun getting to work with founders again on very early product. I took up one more advisory position. One of my contracts, Copper, really intrigued me. I was introduced to its founder, Doug, by Fuel Capital months before. He was on an ambitious agenda to “kill passwords for people.” We built a close working relationship over the next few months, and he finally asked me to come on board full-time. I pondered over it for a while. I wasn’t planning to go all in that soon. I sought advice from some mentors of mine. I was torn between ramping up my contracting and possibly starting an agency, going in-house at a VC firm, or going all in with Copper. A friend of mine, Daniel Burka, made it all so clear. He asked me what I longed for the most. I said I wanted to make real impact again. I wanted to ship an idea to the world. I wanted to take a huge bet on something so ambitious, it was “destined” to fail. I realized I was describing Copper. Agency and VC life could wait a few years. So I joined. Now it’s three of us. We are trying to replace passwords. I think we have a fair shot. Keep an eye out in the coming months.

And that’s 1994 to 2016. Online I experienced more ageism than racism, primarily because I hid my face for a long time. On Twitter, my last name is Nigerian, but you can’t tell. And when I say, “hid my face,” I mean it. My avatar has evolved over the years. It stared as a silhouette, then evolved to a half-shot of the side of my face, to the entire side of my face, to my face. I’d like to think that it mirrored my evolution of my self-identity. I’ve always been self-aware, but now I know myself too. I know my strengths, my weaknesses, and my faults. I know where I’ve come from, and I have a plan for where I’m going. I’ll be dammed if I let people kill my vibe because I look a little different to them. I could care less.

“Online I experienced more ageism than racism, primarily because I hid my face for a long time. On Twitter, my last name is Nigerian, but you can’t tell. And when I say, “hid my face,” I mean it. My avatar has evolved over the years. It stared as a silhouette, then evolved to a half-shot of the side of my face, to the entire side of my face, to my face. I’d like to think that it mirrored my evolution of my self-identity.”

I still experience the “symptoms” of being black in a predominantly white city. Walking down a street, it’s not uncommon to see a woman pull her purse a little closer in, or cross the street before we cross paths. It’s not strange to notice an Uber driver eyeing me through the rear-view mirror. On buses, it’s not weird to see someone stand instead of sitting in the only empty seat that’s next to me. I’ve sadly desensitized myself to these micro-interactions over the years. So that’s why when people ask if I experience racism, I don’t immediately recall these interactions to memory. For me, racism and ageism had to smack me in my face to get a reaction, and everything else was just “how life is.”

But I don’t want the people I work with to ever feel this way. Copper understands this. Yes, it’s only three of us right now, but it’s already part of our identity. We want diversity of people, backgrounds, and thinking. Not to meet quotas, or to look good in Medium articles, but because it’s critical to a company. And because we care. Why would you only want one point of view?

All right. Okay, four main questions I want to dig into. You’ve touched on this, but what do you look for in a job now? What is important to you in your job now vs in the beginning?

One – companies that understand the roles they’re hiring for and how those roles may bleed into others. When you start a company, especially in Silicon Valley, there are things you just do—like setup Heroku, use Stripe for payments, and AWS for file storage. Then when it gets to people, you’re like, “Okay. I need a technical co-founder. I need two engineers. I’m going to contract some designer. At some point, I’m gonna need someone in customer service.” Instead of asking yourself, “What in particular, do I need for my business?” It may not be the same as the company across the street from you. Maybe your co-founder should have a background in customer experience because of the type of product you’re building. Such people don’t hire because a blog told them to. I think there’s a strong correlation between people who hire without understanding the roles they’re filling, and the people they hired leaving. If you don’t know, find out. Your hire will appreciate it. It sets up accurate and attainable exceptions. Alignment is good.

Two – empathy. People who understand that people are people. When you hire someone, you are entering a relationship. There’s this understanding when it comes to co-founders that you’re finding your partner. You’re marrying this person for the next 5+ years. I think the same applies to employees. They’re not just headcount, they’re people, family. The marriage and family correlation is interesting because it also implies that you’re no longer just thinking about yourself. You think about them and their needs. You try to uncover their problems, blockers, and fears. Then you try, to the best of your ability, to mitigate them. This is empathy. Companies that understand this are in a much better position than those that don’t. Their employees feel valued and empowered to do good and to do more.

Three – a plan, or at least a shadow of one. Yes, the future is the future, but if you’re just shooting in the dark believing you’ll eventually hit something, I’ll pass. I’m also curious to see how much of a plan a company is willing to reveal to me. Little reveal is a red flag. This also includes mission. I’ve got to be excited about what we’re working towards, or else what’s the point?

Four – the people. Are we compatible? Sometimes we’re not, and that’s okay. Just so the non-compatibility isn’t a result of you being assholes. That’s not okay.

How do you feel like your background: where you’re from, the places that you’ve lived, your family, the culmination of that and your life experiences, how do you think that that has made you a better designer and even manager?

My dad’s culture is proud, but they are very hard-working people. Recently, a colleague of mine traveled to Nigeria for a project. She came back enlightened. Going, she knew about 419, something that’s synonymous with Nigerians. But she was surprised to learn that 419 represented probably half a percent of the Nigerian population. Yet somehow, it’s something the entire nation is stigmatized for. Being half Nigerian and working in tech, I remember sometimes being wary about revealing that detail. It was the fear of “he got in?” Or “you’re contracting him? He’s 419, man! You can’t trust those people!” Interesting, that never even crossed my mind, until this moment.

They are so proud and so hard-working because they have to fight that stigma every day. That they’re not corrupt people, but that they are people just like anyone else. But also people who have to work a lot harder than their peer to fight a stigma that pertains to such a small percentage of their people. This impacted me in two ways. It taught me to work hard and be proud of my work. Looking at my family, it always impresses me how much harder they had to fight to get to where they were. And as for pride, it was less ego and more knowing when you did good work, then defending it. I’m not the person to defend disproved work, but I am the person to defend good work. My work, my team’s work, etc. Especially when “good” could be backed up with data. Quantitative or qualitative. I’m the person who says “I will go to war with you. It’s not that I’m right, but that this is right. So if you want to fight me, that’s completely fine. But don’t fight something that is actually going to benefit the company or product.” That’s my family’s type of “proud.”

“Being half Nigerian and working in tech, I remember sometimes being wary about revealing that detail. It was the fear of he got in?’ Or ‘you’re contracting him He’s 419, man! You can’t trust those people!”

On my mother’s side, I learned empathy and the power of giving. If you needed $700 and my mom had $699, she would transfer a dollar from her savings and wire you the $700. I’ve done that before. I remember in my first months in San Francisco, a friend was in need of $500 and I had $510. I just sent it. I stretched that $10 a week until payday that Friday. To stretch $10 for a week in San Francisco is hard [chuckles]. Not easy, we’re talking buying a pack of Top Ramen, and breaking the squares into halves to double it. Then trying to get the water to ramen ration just right so it doesn’t taste like flavored hot water, but “soup.” Nowadays I mentor when I can. Andreessen Horowitz does this program where they pair professionals with college students interested in the same line of work. Its a great way to give back. To impart some of the things I’ve learned over the years, in hopes of having that student replicate my successes and avoid my failures. I try to respond to every email I get. If that person took the time to message me directly, it’s only fair I take the time to respond. We’ll see how far that scales though [chuckles]. Inboxes are dangerous. And I still relearn these traits, empathy and giving, everyday from my girlfriend. She’s the most caring person I know outside of my parents. I love her for this. It’s funny, she’s probably the true designer in our relationship.

Empathy is the number one thing for a designer. By definition our job is to remove friction for our customers so the best way to do that is to, in a sense, become the customer and go through your own product. I remember when there was this big renaissance of design thinking a some years back where everyone started saying, “designers, talk to customers!” It’s funny to me, because that sort of thinking should have never been forgotten. If you’re not talking to your customers, what kind of empathy are you employing?

Being exposed to different cultures at a young age also impacted me. Seeing different cultures quickly taught me the power of diversity. The thing about being a minority is, if you grow up in an area where you are the majority, your tendency is to stay there because it’s the one place you feel at home. If you look at areas in the US where African-Americans are dominant, you’ll notice that most don’t leave. And why would they? Most of them are taught from young that the world sees them as second-class citizens. That they are at a disadvantage by default. So that it would in their best interest to “settle in and call this home.” The Brooklyn neighborhood I was born in was such a neighborhood. My neighbors are all still there. Same street, same home, same floor. But I was forced out of that reality from a young age. Now, as a designer, I seek diversity to supercharge my solutions.

Okay, macro now. How do you feel about the state of tech in 2016, like what excites you, what frustrates you?

I’m excited about the evolution of interfaces. Messaging is becoming a new interface, but I doubt it’s going to be the only one. And it’s not going to be that simple. That tends to be the case in tech anyway. We jump into new territory, explore, identify the patterns that emerge, and then turn them into new platforms. For example, I don’t think Slack is the future; I think the essence of Slack is part of the future. I’m excited for these new platforms. They reduce the cost to start something new, and they expand your reach.

Copper, I hope, will one day be such a platform. Every company is trying to build their identification layer. It’s time consuming. We want to eliminate that overhead for them. Then you have companies like Uber and Airbnb where there’s so much contingent upon you knowing that the people on your services are real and trustworthy that they have to invest millions into their systems. Why couldn’t we solve that for them and their customers? Imagine if you just walk up to any service or any door; there’s one simple protocol by which to identify yourself and it’s free to you, convenient, and secure. More businesses are coming up like that. We’re doing it for passwords and identification but there are people doing it for all sorts of stuff. I’m really excited about that.

“I’d like to believe that the companies that rise up from this correction will be stronger in the longterm because they had to work a little harder to raise, make a profit, make an impact, and make a return. It kind of parallels my life.”

I’m also excited for the correction that’s going on in the tech sector right now. People are calling it a bubble; I don’t think it’s a bubble. Let’s use balloon as a metaphor. What happened in the Dot Com era was like someone who blew a balloon too big and it just popped. Then a few years ago when we had another correction, that was like someone who blew a balloon kinda big and someone else poked it with a needle before it popped on its own. I think what’s going on now is like someone blowing a balloon and someone else saying, “ah, I’ve seen this shit before,” then just squeezing the air right out of it; so there’s no pop. Just deflation. That’s our current correction. I’d like to believe that the companies that rise up from this correction will be stronger in the longterm because they had to work a little harder to raise, make a profit, make an impact, and make a return. It kind of parallels my life.

True.

One thing I’d like to see change is our transparency as an industry. When I started out, we were very open with each other. Especially the design community. I attribute that openness to us being able to “level up” in the eyes of businesses so quickly. Or what others call our “seat at the table.” However, in the past year or two, we’ve become more secretive. We’ve switched out that open collaborative-ness for bickering and petty bantering. We talk just as much, if not more via mediums like Medium. But I fear we’re moving forward, slower. Nowadays, the people who are the most transparent with me are my closest friends, and even with them there’s still a filter.

I understand confidentiality and competitiveness, but the opaqueness leads to slower progression as a community due to a lack of knowledge sharing. We’re more on the sharing of Sketch tips than topics we’re all thinking about, but avoiding. Things like diversity at work, women in tech, and processes to advance the sector as a whole, not just our immediate companies. I don’t know how we get back to the good ol’ days. I don’t know, maybe it’s just nostalgia. Maybe it’s just me. But we’ve been thinking about this a lot at The Industry. We’re building a resource for the design community to help. It’s called Playbook and I hope to put it live in the next few months.

One of the biggest things that hurts a business or people is miscommunication. What causes miscommunication is people not being transparent or clear. And I think that good communication unearths topics that need to be discussed. I’m rooting for Techies Project, Helena.

My last question would be, based on the lessons that you’ve learned over time, what advice would you have for other young designers who are hoping to get in tech or are in tech, and are feeling some of the same challenges that you faced?

Let me break the fourth wall here. If you have impostor syndrome, don’t feel like you’re all alone. Everyone has imposter syndrome about something. Anyone who says otherwise is either a narcissist or just lying. Impostor syndrome is different for everyone. For some, it’s weight. For some, it’s height. For some, it’s accent. For some, it’s hairiness. For some, it’s not having a college degree. For others, it’s having a college degree. For me, it’s age and race. I don’t think that will ever change. But the point is to know this. It introduces you to empathy. Just as how you want people to be empathetic to your insecurities, be empathetic to theirs.

Another thing – if you work somewhere that’s eating you from the inside-out, leave. It’s not worth it. I know other industries say to stay for ten years, but you’re in an industry that’s barely 30 years old. We’re blessed in the sense that we can leave a company after a year, and get a job the next day. Most people leave, because they got a new job. We’re one of the few communities where, when you hear someone say, “I quit,” you say, “Congratulations.” In any other industry, it’s like, “Oh, shit, what are you going to do now? That sucks. Do you need a place to stay?” Of course, if you think you can change your situation, persevere and sort it out. Don’t just bounce. But when you can’t deal with it anymore, kill it, before it kills you. If you’re in an industry that you love, don’t let anyone drive you away from it. You’re a techie, stand tall.

“If you’re in an industry that you love, don’t let anyone drive you away from it. You’re a techie, stand tall.”

I grew up in San Jose, California. My family was middle-class. My father was a software engineer, my mother taught school. It was a very conservative household, or at least California conservative. That really textured my world view.

People ask me now, how that affected me being trans, and it’s… well, the thing that you are is such an anathema to the culture you’re brought up in. It’s problematic. I think the biggest impact was that I lacked any real sense of self. I was just trying to be what everybody around me wanted.

Teachers loved me, because I was always doing what they wanted, and I was way more concerned with the adults in my life than my peers. I always did what my parents, particularly my mom, expected. I was always filling particular roles. That really drove a lot of my life in terms of what I did. It wasn’t until decades later, post-transition, where I start to develop a real sense of self. And then I’m think, “Oh, that’s weird—how did I live so much of my life having no real sense of who I was, just trying to be what everybody around me wanted?”

Were you exposed to creativity or technology, or any of those concepts early on?

That’s an awesome thing about the household I grew up in. My dad worked in the software industry. We had computers and game systems in the house my entire life. That was always something we had. We had a Commodore 128. It has the basic interpreter on there. You could write little go-to loop-type things. Actually it was my friend’s dad who had the first computer I ever saw. I was—I want to say—three and a half, maybe four years old, and I’m over at my friend’s house and he’s got this Apple II. It has this green screen. My friend’s dad shows us this vector drawing of a frying pan. You can’t even see it on one screen all at once. You have to scroll or zoom out. I see this and then he shows this little game he wrote of where these little horses race across the screen. Seeing that was the moment where I was thought, “This is the most amazing things I’ve ever seen.” That moment still stands out in my head when people ask me, “How did you get into technology?” That moment was really defining.

Walk me from that moment to working in tech. How did you get into it? What has your career experience been like?

When I first started college I wanted to do something a bit different. I wanted do music for video games. I was strongly pushed by my mother to go into computer science. “You can make all this money doing software.” And so I went into it. It was an interesting thing—I was good at it and I did enjoy it. I think I still regret not following my heart at the time. I pursued a computer science degree, and then started working in the software industry. That’s all I’ve done since. It’s an interesting field. There are times when I love it, and there are times when I hate it.

“I was presenting very gender-queer in interviews. And not getting any offers. Finally, one day, I gave up. I went to an interview without nail polish, no lip gloss. I presented as male as possible. Lo and behold: I got an offer. The thing of it is every time I’ve been brought in for an on site interview, where I was presenting male, I received an offer.”

What are some of the highlights, and proudest moments, and things that have excited you the most about your time in tech?

That’s a great question. I was really proud of my work at One Medical. Before I left there, I took a few minutes and ran a query on the git repository. I wondered, “How much of this code base did I write?” It turned out to be around 40%. During the time I was there, the software team was on average of about five people. Sometimes less, sometimes a little bit more but I was the first developer they hired. Writing that much code could potentially be embarrassing, except that I’m very particular about not writing verbose or excessive code. I write what I need.

I’m really proud of what I did there. I’m proud of the type of work that we did and the direction we were going. That was a really neat part of my career.

Your work has certainly impacted me as a One Medical member.

I look at it, and it’s this was a really big thing that I poured a huge part of my life into, and I look at a lot of other things I’m really proud of, and I feel like none of them quite stand on that same tier. I think I wrote some beautiful code when I was doing device drivers, some really elegant things. I solved some really hard problems, but they just don’t stand up in terms of the long term term impact that they have. One thing exciting about my current role is that it has the same potential for long term impact. We are building tools to fight harassment. To me, that is just as big as doing medical software.

Tell me more about that.

Being harassed online sucks. And I’m working for the biggest player in open source community platforms: Github. They made a decision at a very high level to put money and people behind actually making Github a platform that is safe and inclusive. I’m building up a team; we’ve got a really good foundation in the works. It’s going to be a while until we have real tangible results, and it’s not an easy area. There are a lot of really tricky aspects to it. But those are challenges that I’m excited to rise to. I want to build the online space that I want to have for myself. I want to build an online space that sets the tone for the future. I don’t want just to make this platform good. I want to make it the best of show: a place where voices are not suppressed and that people feel safe.

“I want to build the online space that I want to have for myself. A place where voices are not suppressed and that people feel safe.”

On the flipside, what have some of your biggest struggles been in your career?

The biggest struggle was post-transition, or probably mid-transition, when I was trying to figure things out and just living in a sort of gender-queer life, and I needed to find a different job. I was determined that I didn’t want to work any place that won’t accept me as I am. So I was presenting very gender-queer in interviews. And not getting any offers. Finally, one day, I gave up. I went to an interview without nail polish, no lip gloss. I presented as male as possible. Lo and behold: I got an offer. The thing of it is every time I’ve been brought in for an on site interview, where I was presenting male, I received an offer.

So I got that job. I worked there for a couple of years, and then there were some really negative situations there, however I did manage to transition during that time. That company ended up being a mixed bag. I had some solid support from my peers, but I could’ve had a lot better support from management. I realized, at some point, that the professional relationship had become fairly dysfunctional.

I needed to move on. I started interviewing for other positions. At this point, I was presenting female. It’s a lot different interviewing for a tech job when presenting female.

The bad interviews were not a big deal. If my skill set and approach don’t line up with a company, I expect them to pass. But the good ones… the good ones kept resulting in rejection. When a company decides to keep moving forward, especially when it’s been multiple rounds, it’s clear that they think you are suited for the job. They are spending time and money to pursue you. These companies would get to the end of all of this and then decline me on the grounds of something we discussed as a non-issue in the very early rounds of screening. For example, “We think we want somebody with more such and such experience.” and you’re like, “Wait, we talked about that exact thing during the first phone screen!” Why would you put hours of your employees’ time and mine into this interview process if that thing was an issue?

It’s clear there is a bias at work. A lot of men don’t want to work for or with a woman. On top of that, I never know who might have read me as trans and had their own transphobia come into play. But it’s pretty easy to sabotage somebody in the interview process if you want to. And I’m sure anyone with a non-privileged background faces these exact same type of things where all it takes is, “I don’t think they’re a good fit,” or, “Nah, they made me kind of uncomfortable,” or, “I really didn’t like the way they answered this one thing.” It’s much easier to sabotage somebody than it is to champion for them.

“It’s pretty easy to sabotage somebody in the interview process if you want to. And I’m sure anyone with a non-privileged background faces these exact same type of things where all it takes is, ‘I don’t think they’re a good fit,’ or, ‘Nah, they made me kind of uncomfortable,’ or, ‘I really didn’t like the way they answered this one thing.’ It’s much easier to sabotage somebody than it is to champion for them.”

Let’s dig deeper into that because I’m sure you have a lot to say. You worked in tech for 15 years before you transitioned. So you have tons of experience in the industry. How is life before and after?

I have a much different understanding of privilege. There’s a difference between knowledge and understanding. And to fully grasp the level of privilege I was afforded, it took this very painful experience of having to job search for over a year, and a lot of great interviews that my previous experience said, oh yeah, you have an interview like that you’re going to get a nice offer, you’re going to have multiple offers coming in. You’ll be in this great competitive situation!

Instead I would find that even when things went really well, when I was expecting to receive an offer. I wasn’t sure if I wanted to work at some of these places. I would have been the first woman engineer. Do I really want to be that person? I’ve got a thick skin. I can handle it. I’ll do it.

But then they make the decision for me. They decide I am not up to the challenge of being the first woman. They can’t legally turn you away for that. But they can always come up with some other reason.

These situations brought me to very deep understanding of privilege. It is a much more nuanced and deep and personal thing than I understood before that.

“I’ve had to learn a lot about this privilege thing, and how much I had, and how much I’ve lost.”

There is a huge difference between the male friend who knows, “Oh, it’s not safe for you to walk down this street at night,” They will walk you to your car, all that stuff. They know about that and they do the right thing. But it’s a very different experience when you feel mortal terror. When you have to that walk by yourself, and you have some guy on a bicycle circling up, and coming up towards you, and approaching you, and– There’s a very different feeling and if you don’t have that experience, you’ll never fully understand. You will know. But you won’t understand.

That’s a much scarier place than just not being able to get a job. I’ve had to learn a lot about this privilege thing, and how much I had, and how much I’ve lost.

All of this has impacted me in a professional capacity. I am a huge champion of mitigating and eliminating bias in hiring. We have to really work hard to do this. Fortunately, we have good economic data on why you should do this. Ultimately companies should do this because it’s ethical, but sometimes you can’t always win over a board with the ethical argument. But you can at least win them over with the profit argument.

My experiences have made me a big advocate and champion for how to we empirically cut biases out of these processes, how do we give more opportunities to people from underprivileged backgrounds, how do we make tech a more equitable place? It already has huge economic barriers to entry, for instance, if you can’t afford to have a computer in your house. If I hadn’t grown up in an upper middle class family, would I be in tech right now? Probably not. I might have eventually had access to a computer at school and maybe that would’ve been enough, but it’s very different having had access to a lot of really interesting pieces of technology very young and very early and being able to just play with these things and grow to love them.

Where do you find your support networks?

Professionally or personally?

Both.

Personally, I’ve been very fortunate in terms of the circles of friends that were around me through my transition. The nature of all those relationships changed more than I thought it would. But in pretty much all cases, it was positive – even when that meant the distance in some of those relationships increased. I had a good group of friends to begin with, and that group turned into what I needed it to be. The nature of that circle of friends has changed and who I’m close to and who I’m not, but I have some absolutely amazing people in my life that are there when I need them, and people that I can count on when I feel like I can count on no one else.

“My experiences have made me a big advocate and champion for how to we empirically cut biases out of these processes, how do we give more opportunities to people from underprivileged backgrounds, how do we make tech a more equitable place? It already has huge economic barriers to entry, for instance, if you can’t afford to have a computer in your house. If I hadn’t grown up in an upper middle class family, would I be in tech right now? Probably not. I might have eventually had access to a computer at school and maybe that would’ve been enough, but it’s very different having had access to a lot of really interesting pieces of technology very young and very early and being able to just play with these things and grow to love them.”

Professionally, I feel like I’m only just dabbing my feet in. I’ve only been functioning in the professional world in a gender-variant way and then trans way for like the last four years. I don’t think I really gained much during the genderqueer portion of that, but once I transitioned and was presenting fully female, I have been able to establish some really good professional contacts. I was able to get more involved in organizations like Lesbians Who Tech and connect with other ladies in tech. That’s been very helpful.

It was a huge thing walking into GitHub and finding that there was a built-in support network of ladies there, who are in technology. And having lady managers as peers was actually a big thing. My previous company was too small for me to have any peers, let alone peers of the same gender as mine. That’s been huge. And that’s very recent, but there’s a couple of those people I know that long after I leave this place, they will still support me. I know who to go talk to. There’s experience and depth there.

How do you feel like your life experience has shaped the way that you approach your work?

It definitely shapes how I view the projects I’m working on. I am fortunate to get to take on a project that is directly related to being part of an underprivileged group. I have friends who’ve been deeply harassed for being trans online. Being able to directly work to change that is an incredible professional opportunity.

I have a fairly quiet online profile right now. Because of that, I haven’t faced a lot of direct harassment myself. But I’ve watched this play out in some friends’ lives. It’s personal. It is a very real thing, and being able to do something very real about it is very meaningful.

Earlier we were talking a little bit about really grasping the level of privilege that exists if you are a perceived straight, white, cis male. I’m not white, but I’m “white enough,” at least in the Bay Area. That’s definitely something I’ve started to understand better recently. Maybe some place else, I wouldn’t be white enough.

“We want the a diverse spectrum of candidates. We want to ask all of them questions about diversity, inclusion, and social impact. Those answers matter just as much as the technical questions. It has an amazing way of normalizing a lot of things. On top of that, you’ve now selected for people that are going to be looking for those qualities in others around them. You can leverage the effect people intrinsically wanting to hire others like themselves in a positive way, instead of the typical homogeneous, limiting way.”

These thing impact how I think about hiring and building teams. It changes the types of questions that types of questions you use.

We want the a diverse spectrum of candidates. We want to ask all of them questions about diversity, inclusion, and social impact. Those answers matter just as much as the technical questions. It has an amazing way of normalizing a lot of things. On top of that, you’ve now selected for people that are going to be looking for those qualities in others around them. You can leverage the effect people intrinsically wanting to hire others like themselves in a positive way, instead of the typical homogeneous, limiting way. That way tends to result in teams entirely of people from privileged white male backgrounds. I want other people to care about diversity inclusion. I want other people that are different than me.

I also want other people who might be like me. If you’re the only lady on a team, you desperately want to add another lady to that team. If you find someone who is qualified, you’re going to fight for them. Similarly, like if you’re a person of color, or if you’re a trans. Occasionally will have an interview where the video chat will come up, and I will suspect that the candidate is trans. I will want to give her extra privilege. And I have to actually fight a different type of bias there.  I still have to evaluate her on the same criteria I would any other candidate. Even though personally, I’m like, “I’d love to hire you just because you’re like me.” It’s the same thing. It’s an odd sensation.

Totally.

It ties in a little bit to my experiences, being functionally the same candidate presenting male and presenting female. It’s not that I answered questions differently, or did less well on the technical portions. It was like, yeah I’ve dealt with a lot of identity stuff, but that didn’t change in how smart I was. That didn’t change in how well I do in technical interviews. None of that changed, and yet the responses to me changed dramatically.

Did you experience similar biases when you were employed as well?

Oh,  I can talk about that little bit. In my previous position, it was a place where they all knew me through my transition (which was gradual). Having folks who are not close to you on a personal level see you in both genders is a little odd. I definitely saw ways where I was treated differently after transitioning. In the 15 years of my career prior to transitioning I was never, ever labeled as “aggressive.” Sometimes “assertive,” even “overly energetic,” “frenetic.” All sorts of labels would be applied to me, but never “aggressive.” Post-transition I got that feedback constantly. Especially when I was seeking any form of promotion – where that very behavior that almost guarantees reward of promotion in a male – it was used as criteria to claim that I was unsuited for a particular promotion.

“In the 15 years of my career prior to transitioning I was never, ever labeled as ‘aggressive.’ Sometimes ‘assertive,’ even ‘overly energetic,’ ‘frenetic.’ All sorts of labels would be applied to me, but never ‘aggressive.’ Post-transition I got that feedback constantly. Especially when I was seeking any form of promotion – where that very behavior that almost guarantees reward of promotion in a male – it was used as criteria to claim that I was unsuited for a particular promotion.”

If you get things done as a lady, you’re too aggressive.

Have you had mentors or people that you’ve looked up to along the way?

I have had people who have been mentors in very specific technical areas. I learned a lot about what good code looks like. When I was writing device drivers, I worked for this guy who was a terrible people manager, but a marvelous coder. He wrote beautiful code. That was when I really developed a sense of what beautiful code is. He was the type of person who wrote such beautiful code that almost anything you presented to him, he would not be super happy with. The highest praise was if you put something in front of him and he’d just scowl at it, but he’d have nothing to say. He would be essentially unhappy with it because it wasn’t something that he wrote, but he couldn’t actually come up with any criticism. I learned a lot from that.

I feel like I learned a lot about software management from watching a lot of people do it poorly. It’s an area where I can’t actually talk about a good mentor I have had because it’s a case where I, for the most part, just watched people fumble. I’ve also watched people who fumbled in many areas and then did one or two things right. I’ve tried to glean all these little bits. My strength as a manager is in aggregating all these lessons I’ve learned over years of watching people do things, both good and bad.

There was also a time when I had someone further up in the organization, two levels above me, at the start of my career, who saw potential in me as a leader. She started working with me to develop leadership traits and took time to meet with me one-on-one. That was actually really powerful now that I think back on it.

This was pre-transition for me. I never realized at the time what it must have taken for her to reach that level in that company as a woman. Now I can only imagine the battles she had to fight and what she had to do to get there. What an honor it was that she took time to mentor me.

More recently, I’ve been at a lot of startups and smaller firms. You often have a lot less opportunities for mentorship in those cases. You have a lot of opportunities for growth, but essentially if you’re at too small of a company, you have to look for external mentorship. This goes back to the identity thing I was talking about. If you don’t have a strong sense of self it’s hard to have really solid goals about what you wanna do with your career. Without clear goals it is easy to neglect mentorship and other career development.

It fascinates me that the shift into my actual gender was accompanied by a much clearer set of career and personal goals. Without low level psychological needs being met you can be blind to the higher level stuff. And it’s weird that you can be unaware that those needs are not being met.

How do you feel the state of tech in 2016? You’ve been here for a long time. What excites you, what frustrates you?

The thing that excites me the most, is that the conversation around diversity in tech feels like it is taking on a very vibrant life and it is very real. It’s both data-driven and personal, and we’re seeing that conversation play out, and we’re seeing the beginnings of real change. On the flipside, we’re seeing some really nasty counter-arguments, and we’re seeing a lot of people basically defend this concept of, “No. It’s a meritocracy. If you’re having issues, it’s because you are not good enough,” yet the data says that’s wrong.

“The conversation around diversity in tech feels like it is taking on a very vibrant life and it is very real. It’s both data-driven and personal, and we’re seeing that conversation play out, and we’re seeing the beginnings of real change. On the flipside, we’re seeing some really nasty counter-arguments, and we’re seeing a lot of people basically defend this concept of, “No. It’s a meritocracy. If you’re having issues, it’s because you are not good enough,” yet the data says that’s wrong.”

We’re seeing some companies are stepping up and doing things about it. And my hope is that those companies that are doing something about it don’t just play lip service to diversity and inclusion, but actually really step into that role and say, “We are going to do this really well,” and especially if they then see the rewards and they see economic benefits. That will really help as time moves forward, we’ll see a lot. We’ll see big shifts. If you look at other industries that had deal more direct with affirmative action in the 70s and 80s, you’ll see this indeed happened. Even some industries that are still known for being incredibly sexist. Take Law, which is known for having some really nasty misogyny baked into the system and yet we’re also still seeing that female lawyers are pretty big percentage.

I see tech in a position to actually do better. I want to see tech sidestep the “lean in” approach. Can tech avoid teaching everyone from diverse background to simply behave like the status quo? Can we instead bring a diversity of approaches and personalities into the workplace? The status quo is to expect underprivileged people to to go and behave like the white men in the industry. The more you can behave like these men, the better you will do.

We’re seeing in tech companies that are willing to actually move women into leadership. We do even better when we don’t just look for the women that emulate men but we look for women and people of diverse backgrounds that just are themselves. They bring a slightly different tone and perspective on things, as opposed to just the very stereotypical driven Type A masculine. Type A females are great but they are very different than their male counterparts in terms of their approach and what their goals are. And we’re seeing this type of shift, very slowly. I feel like we’re just at the beginning of this, which is a little painful, but we’re seeing that these shifts are happening and that there are more opportunities.

“The status quo is to expect underprivileged people to to go and behave like the white men in the industry. The more you can behave like these men, the better you will do.”

And we’re definitely seeing a lot more companies trying to just fix their diversity from this big number-game side of it and be like, “Well, we need to hire more women, we need to hire more people of color.” And that by itself is not good enough, because we’ll continue to maintain the reality, most women and people of color leave tech after less than 10 years. If we just hire diversity and we don’t build support networks, these people will be bullied out.

At my current company, I am part of several internal support networks. We are building sub-communities around being Latina or being a woman, etc. We are building these support networks internally in parallel with our recruiting efforts, and that’s a huge deal. And I’m seeing a couple other companies that are doing a pretty good job of that too. They understand that they can’t just hire people from diverse background, because they’ll end up leaving. You have to actually put a support system in for them. And as we see that, we’re seeing this growth and this vibrancy, and you see these just amazing things.

“Most women and people of color leave tech after less than 10 years. If we just hire diversity and we don’t build support networks, these people will be bullied out.”

What are you working on right now, either work-wise or personally, in 2016?

Professionally, I’m really working to build a solid team, to accomplish these goals that I have in terms of fighting harassment and abuse on the GitHub platform. That’s just an exciting thing to be working on, and I’m really excited to be recruiting and hiring for that, and trying to put in really solid processes around how we’re going about building the software we need. That’s exciting.

On a pseudo-professional note, I’m trying to do a lot more speaking and writing about these topics. There’s a reason I’m openly trans on the internet. I made a very conscious decision about that a year ago. I could very well be stealth on the internet. I can mostly be stealth in person, but I made a conscious decision that I have this privilege and if I’m stealth, I give up my voice. And it’s really hard to drive changes solely from the perspective of outsiders who are allies without the voice of those who are actually affected.

One of my big things for 2016 is doing a lot more speaking, and writing about this very topic, and sharing my stories. I’m an empiricist, so I want data on all this stuff. And I get frustrated. There’s not a lot of good data on many aspects of this. In some areas there’s great data. Like we know a lot about gender bias in terms of how it affects interviews. But there’s a lot less about how transphobia, or homophobia, etc come into play. So often the best we have is our stories and our anecdotes. And especially since they’re very real. We may not be able to statistically prove that this is happening, but we can appeal to people’s life experiences and hope they say, “Oh, yeah. That happened. I could totally see that happening more, and that shouldn’t be happening. What can I do about it?” I definitely am trying to use my voice to make the world a better place for anybody from a non-privileged background.

I would love to hear you speak. You’re so eloquent in everything you’ve said here.

Thank you.

Where do you see yourself in five or ten years? Do you think you’ll still be in tech?

Probably. I could see using some of my work, in terms of the trust and safety, could move me someplace different. But, if I do that it would still be someplace clearly related to these very issues of making sure that people have safe and inclusive spaces and that we’re building these types of places both in real life and on the internet. If I stay in tech I definitely hope to tackle some level of upper executive-style work within the tech industry. I think I have a lot to draw on in terms of that, and that’s a direction I would like to see my career go long-term.

What advice would you give to folks going through similar struggles or coming from similar backgrounds to you in tech?

That’s a hard one, because there’s a degree where I want to say,”Don’t give up.” And there’s another part of me that feels like that’s the most flippant advice in the world.

It was incredibly emotionally destructive for me to deal with the rejections of interviews I knew went well. I expected to be rejected for something that didn’t go very well, or I could tell we were just on different pages regarding management style. But the interviews where it was clear that we synced and it was clear that there was a good match and a good fit…. To get turned down for those was just unbearable. And no, not just once or twice — the first couple times you dismiss it. By the third and fourth time, it was really so incredibly emotionally destructive.

It’s hard for me in good faith to say, “Just stick it out, it’ll be fine.” We need diverse people in tech. I don’t know what the answer is there. It makes me sad that that’s the case.

“I’m an empiricist, so I want data on all this stuff. And I get frustrated. There’s not a lot of good data on many aspects of this. In some areas there’s great data. Like we know a lot about gender bias in terms of how it affects interviews. But there’s a lot less about how transphobia, or homophobia, etc come into play. So often the best we have is our stories and our anecdotes.”

We need to keep fighting to eliminate these biases and make sure people really do have a fair chance. Yet I know that not every company is trying to do that, and so I don’t know what the answer is. There’s a school of thought out there advocating that underprivileged folks should just be the entrepreneur and go that route. But then you have the problem of, yeah, you can do that, but the bias is then going to happen to you at the funding level.

The best I can do is try to leverage the privilege in my life to improve these situations. I have this privilege, I have a job, I have a position, I have authority. I can use that to try to fix these problems from that side. What do I tell someone who is young and up-and-coming? I can say, don’t even apply at the places that are shitty?

[laughter]

I don’t know how you make it. We’ve built a system that is so just difficult and ultimately cruel. I’m really hoping to see some of the very big players build out better programs for early engineers, early career engineers. I’m also hoping to see them build out better support systems for people in their mid-to-late career so that they can bring in women and people of color that have managed to survive and make it a good place to be. We have to see some big changes, both from start-ups and also from the big players, the big employers, the ones that employ tens of thousands and not just a few hundred here and there.

I was born and raised in Boston. My parents are immigrants from South America, and I am the first generation American in my family. I grew up in acity called Somerville, a really nice area outside of Boston that’s been getting more attention lately. Mostly, it’s experiencing gentrification, partially led by Harvard, but ia nice diverse city made up of immigrant and working class families.

When my parents left Brasil for the U.S., they left behind interesting lives and successful careers there. A lot of people assume that every immigrant who came to the US was looking for a better life or to chase the “American Dream,” but my parents didn’t have much of a choice. My older brother needed open-heart surgery and the only hospital successfully operating on children was in Boston. So my parents came to the US so he could get the life-saving surgery and care that he needed.

“When my parents left Brasil for the U.S., they left behind interesting lives and successful careers there. A lot of people assume that every immigrant who came to the US was looking for a better life or to chase the “American Dream,” but my parents didn’t have much of a choice. My older brother needed open-heart surgery and the only hospital successfully operating on children was in Boston.”

Not knowing English or knowing anyone here, they realized pretty quickly that it was really hard work. With few options, they started their own house cleaning business. They made flyers that read, “We put your house to shining.” I was too young to really understand but when I found a copy of the flyer when I was about 13 or 14, I thought it was amazing. I showed my mom and we laughed for a moment, but we then talked about how hard it was for her to be a domestic worker.

After my parents divorced and my mother switched careers, I saw her blossom into this really awesome woman. She started her experiences and background to make positive changes around her. She became an advocate for immigrant women, survivors of abuse, domestic workers and became a bit of an organizer.  As a kid, I didn’t fully appreciate what she did. I just assumed, “Oh, this is my mom. This is what all kids do. They go to these rallies, right?”

In your pre-interview that by the time you were 18, you already dealt with depression and experienced homelessness, you survived domestic violence, and you’ve given birth to a child.

A lot happened in my young life and I think when young people share their tough experiences, society’s first instinct is to blame their parents. My parents loved me, cared for me, and worked hard to do a lot for me. The issues I faced were complex and layered and the reality is that they were struggling too.

Sometime in my journey through middle school, I became depressed. I wasn’t sleeping, I was anxious, and I was having a hard time finding myself. My doctor was hesitant to label it “depression” and convinced my mom to take me out of my current environment to see if a change of scenery for an extended period of time would help me. She did. I spent 2 ½ months in Brasil with her and my brother learning more about my culture, visiting family, riding horses, and being away from what felt like a negative and toxic environment. But the trip had to end and I eventually had to come back home.

I think my parents were convinced that my peers were driving me into a downward spiral so they decided at the last minute to enroll me into a private catholic school in the next town over. Horrified, I spent days crying in my room. The new school was supposed to be a new chance for me to be around people who were smart and driven. The problem was that dozens of other parents felt that way too and sent their kids to this school thinking it would resolve all of their core issues. It ended up feeling like a space, a breeding ground, for young people with complex issues who were turning to drugs for relief.

“Since it was a Catholic school, we definitely did not receive information about making healthy choices around relationships, dating and sex. We weren’t provided with information on how to keep ourselves safe or recognize signs of abuse. We, the girls, were just expected to keep our legs closed.”

And since it was a Catholic school, we definitely did not receive information about making healthy choices around relationships, dating and sex. We weren’t provided with information on how to keep ourselves safe or recognize signs of abuse. We, the girls, were just expected to keep our legs closed. And the message at home wasn’t much different. I was the only girl among my siblings and often felt the burden of supporting my mother to help provide for the family. I did a lot of cleaning and cooking and my mom reminded me that as a kid, she was already the head of the house, hand-washing everyone’s laundry, cooking dinner every day and responsible as the head caregiver for her own 4 siblings. Her expectation for me was not to be an adult, but I was expected to be responsible.

“Having a lot of responsibility and never really getting the help I needed to cope with my issues made me a vulnerable target.”

By the age of 14, I was in school full-time, involved in a ton of extracurricular activities, babysitting and working as a hostess in a local restaurant so that I could help pay bills. Every month, I would help my mom sort through the bills and make phone calls to service providers to dispute charges or request help. My mom knew how to do this, but she explained to me that she felt her english was so bad that people would never take her as serious as they would take me. That even though she was a woman in her 40s, her broken english meant a child with no accent would have more respect in the US. And she didn’t get this idea from nowhere, it came from years of people telling her that they couldn’t understand her or that she should leave the country if she can’t learn english properly.

Having a lot of responsibility and never really getting the help I needed to cope with my issues made me a vulnerable target. During a very troubling time in my life, I met  someone a little older than me who maneuvered his way into my life by offering what a young vulnerable girl needed at the time: support. And this isn’t an uncommon tactic. People can sometimes sense when someone is going through something or feeling very vulnerable, but there are certain kinds of people that feel that and use it to prey on them.

“During my junior year of high school, I found out that I was pregnant.”

During my junior year of high school, I found out that I was pregnant. I thought, “Oh my God! This can’t be happening to me. I go to a Catholic school! My parents will hate me.”

To of add a layer to that, I knew that my mother was also a young mom and then my grandmother was a young mom, that my aunt was a young mom, and it continues across several generations. And since they are Latinas, I like to talk about the reality of teen pregnancy in our culture. In our communities, young motherhood isn’t framed as a negative outcome. At the same time, young motherhood isn’t the expectation. But in a culture where women are denied access to quality education and/or prevented from pursuing careers, the next step in life for young women is marriage and/or motherhood. And that was the story for a lot of the women in my family. There was no reason to wait until 30. If you didn’t intend on going to college or establishing a career, what are you supposed to do for over 10 years between your high school graduation and the “ideal” age of motherhood. But what happened, at least this is how I see it, my parents assumed that because I was born in the US, that I would adopt American cultural norms and beliefs.

But I got pregnant at 17 and the first adult I told was my school nurse. In theory, you would think the school nurse would understand, what is essentially, your health condition and provide you with unbiased advice. You assume that as a medical professional, they will help you. Being in a Catholic school made my pregnancy a little more complex. What I heard was, “You already made a mistake so you can’t make another one.” Of course, this was the discussion around my reproductive choice and instead of providing me with all of my options and going through what the best choice was for me might be, I didn’t have a choice. Despite that, I walked away thinking about the reality that I could still get an abortion and no one would know. I could just do it, tell no one, and start all over. But I think my nurse knew that, so she told all of my teachers about my pregnancy. So here I am: pregnant, junior year in a Catholic school and I had nuns and teachers pulling me aside to tell me what decision I should make and shouldn’t make. “Oh, one sin can be forgiven but not two.”  

“But I got pregnant at 17 and the first adult I told was my school nurse. In theory, you would think the school nurse would understand, what is essentially, your health condition and provide you with unbiased advice. You assume that as a medical professional, they will help you. Being in a Catholic school made my pregnancy a little more complex. What I heard was, ‘You already made a mistake so you can’t make another one.'”

I was young and really relied on the acceptance of the people around me. And I really believed that if everybody knew that I was pregnant, then noticed my belly wasn’t growing, that they’d know what I did. I thought they would judge me and I thought I would end up regretting the decision. I was stuck in a position where I couldn’t make the best choice for myself. And maybe the choice would have still been the same in the end, but at that time my judgment was so clouded. So, I decided to continue with my pregnancy.

I told my mom first and she couldn’t believe that her daughter was pregnant. And I don’t blame her. There’s an assumption and a false stereotype about what kind of girls get pregnant. And I didn’t “fit into” that stereotype as a responsible daughter, honor roll student, and class representative. My parents were upset and I can understand why. They worked really hard in a new country and fought so hard to shed themselves from the stereotypes that Latinos face in the United States. Then they discover their teenage daughter is pregnant. It felt like the ultimate stereotype and they didn’t support me. They kicked me out that day and I had to pack my things and move in with my boyfriend.

Oh my gosh.

That period was really hard for me, because I was leaving a home where I felt safe and in with someone who I barely knew. I was isolated from the only support system I ever had.

“My parents were upset and I can understand why. They worked really hard in a new country and fought so hard to shed themselves from the stereotypes that Latinos face in the United States. Then they discover their teenage daughter is pregnant. It felt like the ultimate stereotype and they didn’t support me. They kicked me out that day.”

To make things more complicated, he was a marine getting ready to leave for training. Before my first trimester ended, he was already gone and for the next 6 months, I was completely alone. And since I was no longer living with my parents, I finished my junior year of high school and enrolled as a senior in a new public high school.

In September of 2005, I started my last year of high school as the new pregnant girl. To top off the experience, my new guidance counselor learned of my pregnancy and decided to remove me from my honors classes and put me in slower-paced classes. When I asked her to put me back into honors, she told me that I probably wouldn’t even graduate and that I should just try to get by in the lower classes – as if she was doing me a favor. But my pregnancy wasn’t impacting my ability to function in class, and I wanted to learn and I wanted to feel challenged. I wanted to continue on the path that I was on, and I couldn’t do that if people were making decisions for me without involving me. Luckily someone else in the school knew about the situation and really wanted to be an advocate for me, and so she stood up for me and said, “Put her back in honors. If it gets to the point where it’s not going well then that’s a whole different story, but put her back in honors.” And they did.

The assumption is that our peers are the ones who will pick on teen moms or give us the hardest time, but they were actually the most supportive to me. My classmates were amazing. They brought me snacks, they carried my books, and they let me cut the lunch line. They asked me questions about what my experience was like, they offered to babysit, and they spent time with me so I wouldn’t feel so alone. In school, it was teachers who were judgmental and mean.

“Older women are celebrated, supported, and the people around them will help in any way they can. That doesn’t happen for teenage girls. When we are in pain or afraid, we don’t get help. We’re told our pregnancies are punishments and this is the consequence.”

These small gestures helped so much. I was too proud to ask for any assistance, because I didn’t want to be the stereotype of what a teen mom was. I wanted to prove people wrong because I often heard, “You became a teen mom because you wanted free stuff, you wanted handouts.” That fear of judgment actually put me in worse situations because– when I should have asked for help and when I should have gone to people to tell them what was going on, I didn’t want to, because I was afraid they were going to say, “I told you so.” or “You’re just like all teen moms.” People really don’t know what it’s like for a teenage girl to be pregnant, unless you were one yourself. Older women are celebrated, supported, and the people around them will help in any way they can. That doesn’t happen for teenage girls. When we are in pain or afraid, we don’t get help. We’re told our pregnancies are punishments and this is the consequence.

My daughter’s father returned four days before I went into labor. During my daughter’s delivery, there was a moment when I started panicking. Her birth was recorded so I can still watch the moment when I went from grunting to crying to staring at the ceiling. See, throughout my entire pregnancy people said things like, “This child’s going to ruin your life. You’re life is over. You’re not going to be able to do any of the things you ever wanted to do. This is the worst thing that could happen to you.” So as I was giving birth to her, I started panicking, because I realized I was giving life to the person who would end mine. And how do I love someone who is meant to ruin my life?

Because of that experience and internalized belief, I had a very negative journey through the first few years of motherhood. I was diagnosed with depression and prescribed anti-depressants. To make matters worse, I was in a horrible relationship and was constantly told that teen moms like me are never taken serious and that no one wanted to love a woman with stretch marks and a baby. There was no one cheering me on, no one who believed in me, and I felt entirely alone.

At the same time, I was constantly facing barriers in school. The school was only required to offer me tutoring in 4 of my 7 classes during maternity leave. It was the minimum required to help me simply pass the school year. But I didn’t want to just pass, I wanted to do well in every class and graduate with a good GPA, like I would have before my pregnancy. So my psychology teacher volunteered to come to my house every week and tutored me in all 7 courses. She brought my exams and quizzes and held my daughter so I could take them. She held my textbooks while I breastfed and was always proud of my progress. Returning to school was tough, the other teachers weren’t as fond of me or my “situation.” They would refuse to meet with my after school for help and embarrass me in class. One teacher told me in math class that there was no way I could catch up, so I proved her wrong by acing the class.

“I even had to fight for things like the right to pump breast milk twice a day. The school didn’t want to let me because they thought I was trying to find excuse to get out of class. Right. Because what every 18-year-old girl wants is to like skip her lunch break so she can be sit in the nurse’s office pumping milk and nibbling on crackers.”

But I even had to fight for things like the right to pump breast milk twice a day. The school didn’t want to let me because they thought I was trying to find excuse to get out of class. Right. Because what every 18-year-old girl wants is to like skip her lunch break so she can be sit in the nurse’s office pumping milk and nibbling on crackers. That is so much fun.

I dealt with a lot of people who constantly tried to limit my choices and my future. Then closer to the end of that semester, I went back to my guidance counselor’s office to ask if she could help me look over college applications. Most of my friends had already applied and had already found out where they were going, and I was late but wanted to do make it happen. Her response without even making eye contact with me was, “Well, let’s see if you even graduate high school first.”

God.

I walked away from that and thought, “Oh, she’s probably right. I probably won’t be able to do this, and I should probably take things one step at a time.” So I didn’t apply for college. Now, the good news is I did graduate high school on time and I did walk the stage with my class. I did get to stay in my honors classes throughout the whole year, and I did well in all of them, despite being a teen mom. I think, actually, I did better in school because I was a teen mom and because I had something else motivating me to do even better.  But people outside of me and my daughter’s life didn’t see that.  

So, you graduated, you didn’t go straight to college—what were those next few years like for you?

When I was in high school I really, really wanted to go to med school. I wanted to become a psychiatrist. Having been a young person who coped with depression, I knew what people like me needed and I understood the differences in cultural understanding of depression. For example—parts of my family are really religious and there have been times people said things like, “You’re not depressed, you’re just dealing with something. Pray to God. You’ll be fine.”

“No one in my family filled out a college application. I had no idea of what that process was like, I had no idea of what you were supposed to do, when you were supposed to do it, what was normal, what wasn’t.”

I knew at a young age that this was not right.  I just couldn’t articulate or figure it out, but I wanted to become a psychiatrist so that I could serve and help young people, like me. Now, the idea of going to med school was really overwhelming because again, my parents were immigrants and they weren’t citizens, and they weren’t in the best financial places, and no one in my family had ever gone to college. So I knew that first, they wouldn’t able to co-sign loans for me and I felt overwhelmed at the thought of the expense. And even if I chose another career, I didn’t know how to navigate the process.

No one in my family filled out a college application. I had no idea of what that process was like, I had no idea of what you were supposed to do, when you were supposed to do it, what was normal, what wasn’t. The idea of a young mom with no support becoming a psychiatrist felt way too overwhelming. It felt unattainable. So what I did was, after I graduated, that summer I looked at local state and community colleges that would accept late applications.I might not be able to become a psychiatrist right away but I can start the process  by becoming a nurse. It seemed a little more attainable and promised a guaranteed job.  So I applied for college, started in the fall, finished off my prerequisites, and prepared for a career in nursing.

“I entered college with a new identity. I didn’t tell anyone that I was a mom, including my professors. I just so badly wanted to be treated the same as everyone else.

I entered college with a new identity. I didn’t tell anyone that I was a mom, including my professors. I just so badly wanted to be treated the same as everyone else.  The problem was that I was still facing unresolved issues and an internalized belief that I was not valuable. So I didn’t ever explain anything to my professors and by my second year of school, I dropped out. I didn’t have reliable childcare, I was still coping with depression, and I was working a full-time job and living on my own.  I decided that if I was going to accomplish anything, I needed to take care of myself. That I was going to focus on being a good mom and practice self-care.

Wow. How did you end up in tech?

That’s a great question. It’s quite a little bit of a journey from that point to getting into tech. I don’t have a traditional tech background, as I think a lot of people do out here. After I took this break from school I started focusing on myself. I started to deconstruct and redefine what it meant to be a young woman and single mother in today’s society. I started talking to other young moms—which was life-changing—because it really helps when you don’t feel as isolated.

I started realizing that thousands and thousands and thousands of young women across the country are dealing with the same exact thing. 100,000 teens give birth every year—more than 80% were unplanned—and so many of them drop out of school, or feel pressured to leave or didn’t receive the support that they need to stay. Yet, many some of them share that it’s not actually pregnancy and parenthood that makes their lives hard, as we often hear, but it’s actually the way people treat us. It’s the way that our educators treat us. It’s the way a lot gate-keepers treat us. It’s the ways in which people invalidate who we are as just women and humans in society. The minute we become young parents we’re labeled as irresponsible, and told we’re awful people, and that we should just be isolated and not exposed to the general public because we’d cause an “epidemic.”

So I began looking at ways to counter-message the false reality that young mothers are not productive members of our society by leveraging the power of new tech, like social media. My first time trying out this theory was with the Children’s Hospital in Boston, where I developed a comprehensive strategy for using new tech to eliminate the feeling of isolation among over 500 young parents in Boston. That opportunity led to a hire at the Brigham and Women’s Hospital where I expanded the program to make an impact on reducing health disparities and improving health outcomes in the lives of young mothers of color in Boston. Then I was hired by  the Massachusetts Alliance on Teen Pregnancy where I worked on a $5M dollar grant from the CDC to reduce the teen pregnancy rate in two cities by 10% in five years. In a few months, I helped develop a social marketing campaign for two cities. We reached our 5-year targets before year 3.  

“Initially, I thought, ‘There is no way I want to work in tech. I can’t give into that culture or space because, well, it’s tech.”  I thought, ‘I can’t do that. I can’t be for racial justice and reproductive justice and work in tech. That doesn’t make sense.'”

While all of this was happening, I also started a grassroots campaign called #NoTeenShame to change a terrifying message that organizations like the Candies’ Foundation and multi-millionaire CEOs like Neil Cole share with teenage girls about sexuality and choice and I partnered with six other young moms from different parts of the country for its launch and within a week, it went viral and we were being featured in everything from Ms. Magazine to Business Insider.  It was exciting for people to see seven young moms of color across the country were starting a campaign against this multimillionaire CEO. It went viral to the point where he caught wind of it and wrote a response on The Huffington Post about it. It was not the response we were hoping, but it was a win for us none the less. Once that happened, we started getting contacted by just about every organization in the United States that was working with young people to get our insight on how to do the work better and more effectively. We got really busy really fast and people just started reaching up to us and asking, “Well, how can we replicate the models that you guys have used in your respective organizations to help young people? What should we be doing differently?” The series of all those events led to me developing strategic frameworks for using new technology for social impact and finally presenting at a tech conference here in San Francisco last year.

For a long time I envisioned tech as the enemy—I’m a reproductive justice activist. I’m a racial justice activist.

When I wased in San Francisco, I met someone on the executive team at a startup called Honor (where I work now) who was interested in the work that I did,how I accomplished it and how creative I was in using very little resources to accomplish a massive goal. And so we started talking, and I met other people on the executive team. Initially, I thought, “There is no way I want to work in tech. I can’t give into that culture or space because, well, it’s tech”  And so coming into this space, I thought, “I can’t do that. I can’t be for racial justice and reproductive justice and work in tech. That doesn’t make sense.” I had this assumption that social justice didn’t fit into tech, but I think that’s because I based my opinions on the negative stories I heard on the east coast. But once I met the people that were leading the company, I realized that so much of what I assumed about the people in Silicon Valley were wrong. But also that someone like me can still be in tech and be a valuable asset to the work. And as weird as this sounds, I do think I found that special startup that actually developed a really good frame from the very beginning of how they do work. So, I waited a while and I thought about it, went back to Boston, and decided to pursue the opportunity. I thought to myself, “Oh my god. I was 27 years old. I have a daughter. I’m a single mom, and the only family that I have in the US are just four people who live in Boston. And now I’m accepting the  opportunity to move to San Francisco to work in tech.” And that was hard to wrap my head around.

It was actually my mom who said, “Natasha, you can do this. You’ve overcome way harder things in your life.” When she was 27, she was on her way  to the US for a completely different life. And so she said, “I did it, and I’m not saying that we’re the same. But you can move across the country to pursue this. You can do this.” She also reminded me that I had to think about my daughter who’s really interested in science and has been going to all these science clubs. I now have an opportunity to actually be in this field, to actually be in tech, and provide her with an inside view of what this world is really like. She can watch me go through this process and this journey, and she’s going to see how hard it is. She’s going to see the good and the bad, but she’s going to see it. And she’s going to appreciate it. So, it was a combination of those things that made me decide to say yes to the new field and the big move.

So, what was Silicon Valley like for you when you first got here?

There’s been positives and negatives. One of the things that I actually had to overcome when I came here is how fast everything moves. It’s really fast-paced. Everybody told me it was like this, but it was ten times faster than what I’d prepared myself for. And initially, it was really hard, but I also had a really supportive group of people here where they were willing to help me adjust.

“I love that when I’m having lunch and sitting at a table with people who are amazing engineers, or accomplished healthcare professionals, and talented organizers. And we all sit at a lunch table enjoying each other’s company and discussing the very different experiences we’ve had—and how those diverse experiences shaped such an incredible company.”

The other difficult transition is coming from a space where I talked about racial and reproductive justice 24/7 without filtering myself. Prior to this role, I went to networking events where we introduced ourselves by identifying which pronouns we prefer, the issues we’re working on and how we identify. It’s much different here where I’m often asked to introduce myself by position, educational background and accomplishments. And even when I went to events centered on inclusion, I didn’t feel included. How are so many companies  hosting an event on improving inclusion in the tech sector, hosting in spaces that are difficult to access, and not offering things like child-care?

What has been most exciting of activating for you in your work here?

What’s been most exciting is the people that I get to work with. I love that when I’m having lunch and sitting at a table with people who are amazing engineers, or accomplished healthcare professionals, and talented organizers. And we all sit at a lunch table enjoying each other’s company and discussing the very different experiences we’ve had—and how those diverse experiences shaped such an incredible company.

Despite growing up 5 minutes from Harvard and 10 minutes from MIT, I felt so disconnected from people in tech. They seemed so unreachable and different. And I didn’t always see them as the people I wanted to aspire to become. The Harvard grads were the ones moving into our community, pushing families out of homes, so 5 or 6 students could move in, bumping up rent from $1000 to $3000, a profitable idea for landlords. So I witnessed how the growth and expansion of schools like Harvard led to the immersion of grad students into my community, which meant the immigrant and working class families had to leave.

“Despite growing up 5 minutes from Harvard and 10 minutes from MIT, I felt so disconnected from people in tech. They seemed so unreachable and different. And I didn’t always see them as the people I wanted to aspire to become.”

That played a role in how I perceived tech, even though I was using platforms like Facebook. It didn’t occur to me that someone not too distant from me created this. To the teenage me, it was just something that was created by someone somewhere. It took years before I learned that it was created 5 minutes from my house.

It was cool, but it frustrated me because I felt like there were so many issues impacting young people in Somerville and Cambridge and no one seemed to care. And it was frustrating to see people come from all over the world to study here, learn from the community, then leave forever. Now that I’m on the inside, I see how difficult it is to create tools that are genuinely helpful to people—especially if it’s for people of low-income. And it’s frustrating.  

I’m curious to know how that experience, seeing that tech ecosystem in Boston affects the way that you feel about the state of tech here right now?

Boston’s tech scene is very different than it is on the west coast. It’s thriving, but in a very different way. So although I was involved there, it didn’t help much when dealing with imposter syndrome. I think we often frame and consider imposter syndrome as a one time occurrence that we overcome. But what I learned is that it’s a life-long issue that you’re constantly battling. See, when my Boston friends learned the news of my move to San Francisco to work for an Andreessen-Horowitz backed startup, they were amazed. To them, I was doing what so many wished they could do and I was supposed to feel like “I did it!” And I did, but there’s still the reality that you’re constantly needing to be ahead of everyone else and doing incredibly well. I love the field and where I work, but there’s internal self-created pressure to make sure I’m outdoing myself.

“When everyone around you has very similar background, you can sometimes still feel like an outsider. I didn’t have the typical college experience, I didn’t have those amazing internship opportunities, and I didn’t have parents who could introduce me to really cool people or get me jobs or even read over my essay to see if they were grammatically correct. Growing up, I had to do and figure out all of those things on my own.”

But when everyone around you has very similar background, you can sometimes still feel like an outsider. I didn’t have the typical college experience, I didn’t have those amazing internship opportunities, and I didn’t have parents who could introduce me to really cool people or get me jobs or even read over my essay to see if they were grammatically correct. Growing up, I had to do and figure out all of those things on my own. So part of the culture shock is being lost in the conversations centered around privilege.

The other thing too that I notice out here that never happened to me before is we meet people and they’re constantly extracting from you. “What are your thoughts on this?” and “What are your thoughts on that?” And I’m hesitant to share information because also as a woman of color and having done really great work over the past decade I’ve constantly experienced situations where people with power will take a little bit of information from me and then turn it into something that they get credit for. And so, there’s this constant erasure that happens to young woman of color, so I’m hesitant to engage based on this historical experience. Especially if they’re not being transparent with me.

“I’m hesitant to share information because also as a woman of color and having done really great work over the past decade I’ve constantly experienced situations where people with power will take a little bit of information from me and then turn it into something that they get credit for. And so, there’s this constant erasure that happens to young woman of color, so I’m hesitant to engage based on this historical experience.”

The other piece is that I have internalized stigma as a teen mom and it pops up from time to time. I tend to find myself avoiding conversations that might turn into a discussion about me being a single parent that turns into facing a series of invasive questions. Because it happens. Too often. And it’s not intentional, but their unconscious bias just starts surfacing, and they ask, “Well, how old’s your kid? How old are you? Oh my God, that mean’s you were in like…” You literally see them every time look up, do the math, and they’re like, “Oh my god, you were 17! What was that like? What did your parents say?” And it just turns into this whole dialogue that I don’t want to be a part of. Interested in my story? Go read about it or watch Gilmore Girls. I don’t want my struggles to be the center of discussion, especially in a society where we were made to believe that teen parenthood is a bad thing.

How has everything we’ve talked about, both your experiences in tech so far, and your upbringing, and all of your cumulative experiences, how does that effect what is priority to you here? What is priority in a job, what is priority in what you’re trying to get out of Silicon Valley?

So it’s actually really interesting, because I feel like a lot of people out here are really focused on long-term planning. There’s nothing wrong with that, it’s necessary, but I feel like my goals are very different than a lot of people in my position. And that has a lot to do with the reality of how much progress I’ve already made in the past decade. I’ve met and exceeding so many of my own expectations for this period of time and I wanted to spend time acknowledging that and perfecting and improving everything I do now. It doesn’t mean I’m not going to push myself to grow more. I’m focused on ensuring what I do on a daily basis is amazing and meaningful—I’m focused on leaving behind a legacy that my daughter would be proud to share with her grandchildren.

I think a lot about how my mother’s move to the US changed the entire future of our family. So I can’t help but wonder what amazing choices I can make that will continue to do that. If I have the power to shape an incredible future generation, I will do that. And I want to be present today, enjoying my life and my daughter’s life—not waiting for happiness in the form of monetary success.

I’m curious to know how much you’re balancing what you’re working on now and the activism that you’ve been involved with so long, and what it’s like being a part of both of those worlds, especially in the context of San Francisco.

After accepting a position in tech, I thought that I could still be an activist and a writer. But I realized that it was going to take a lot of my mental capacity and energy to adapt to startup culture and do my work really well. Although my personal work is always with me, I knew that I moved across the country for this amazing opportunity and I wanted to dedicate as much a possible to meeting my expectations. Prior to my move to San Francisco, I was presenting at different conferences and organizations across the countries and being asked to do a lot of consultant and advisory work. I had to start declining a lot of those opportunities. And I had to adjust to the realization that nobody in this sector knows me, which is different than Boston.

“Prior to my move to San Francisco, I was presenting at different conferences and organizations across the countries and being asked to do a lot of consultant and advisory work. I had to start declining a lot of those opportunities. And I had to adjust to the realization that nobody in this sector knows me, which is different than Boston.”

Outside of work, my only priority is being a really amazing mom. That can be challenging when you’re working in an environment where working moms aren’t the majority. The ways in which you use and prioritize your time is different and participating in after-hours anything is often a challenge, even though they’re usually necessary and important. Childcare is an obstacle when you’re a single mom in a state where you have no family and feel like you’re already spending too much time away from your kid.

How’s your daughter liking San Francisco?

She loves it but hates the hills. I hate it more than she does honestly but she likes it here a lot. Ha!

She’s really thoughtful and friendly so she made a new best friend within her first week in school. It’s been super easy for her in that way. And like I mentioned earlier, she’s now really interested in Science. Back in Boston, she participated in many different science clubs and programs. It helped expand what her understanding of science was and she became really excited about the opportunity for me to work in tech. And I’m glad she felt good about the choice because I hope she can face an obstacle one day and remember that, “My mom went through this too.” And we have deep conversations about girls in STEM and what it’s like to be a girl in a lot of the science programs. It was interesting to me that she wasn’t interested in the field because of the cool “perks” but because she sees this space as the space where she can do amazing things. Her mission is to promote eco-friendly lifestyles and find a cure for Alzheimer’s. After my grandmother passed from Alzheimer’s, she felt deeply connected and spent a year asking me countless questions. She knows we’ve created tech to do some amazing things and hopes she can do something amazing too. And I’m going to nurture her interest in science until she does exactly what she wants to do.

“I think a lot about tech’s impact on marginalized people, and not just how they use the service but how they actually can be included in the development of new tech.”

How do your friends and family from home feel about how far you’ve come and all you’ve accomplished?

They’re really happy for me. Actually, I had one friend who she really said, “Natasha I think you did everything you could here. You literally accomplished everything and there wasn’t a better next step than this.” My mom is really proud.

How you feel about the state of tech in 2016? What excites you, what frustrates you, what would you like to see change?

I think a lot about tech’s impact on marginalized people, and not just how they use the service but how they actually can be included in the development of new tech. This is where my previous experience overlaps with what tech is missing—the ability to always center the needs of the people they’re targeting. When we’re talking about young people, I’d love to see them getting the support and resources they need to turn their innovative ideas into reality.

“As a mother in tech, I also faced the reality that so many of the programs meant to nurture girls’ interest in STEM are not easily accessible. The programs are often replicating the very same systems that worked for people already in tech. I’ve found myself feeling like the burden falls on parents to fix the pipeline issue and get girls into STEM.”

As a mother in tech, I also faced the reality that so many of the programs meant to nurture girls’ interest in STEM are not easily accessible. The programs are often replicating the very same systems that worked for people already in tech. I’ve found myself feeling like the burden falls on parents to fix the pipeline issue and get girls into STEM.

One example is my daughter had science club on Saturday mornings, and it was at a college campus, which has its pros and its cons. The pro is that it’s great to send girls to a college to see what that environment is like. The con is that it’s often inaccessible for a lot of parents and families and it requires a lot of commuting. And then the classes are so short that parents, can’t just drop off their kids at the program and then go home or doing something else and then come back. They must sit there waiting. So parents are asked to spend a few hours every weekend getting their kids to this program, waiting for them, and then commuting back home. And that could be a barrier to some. The other barrier, of course, is a lot of these programs are really expensive, so if you’re creating programs that are supposed to improve diversity but they’re really expensive, only the people who make enough money to afford it it will be able to get their children into it. There’s usually a financial aid or scholarship application, but it puts the burden on parents who are now of low income to prove to the program that their children deserve a chance. Now you have moms and dads or grandparents, being asked to fill out applications that ask invasive questions about their finances.

“They’re asking parents who are already dealing with a lot to prove and to open up about these issues with people they don’t even know, so that their kid can have an opportunity that they deserve. What if parents don’t even speak English or what if they’re undocumented and don’t have tax documents proving they are of low income?”

They’re asking parents who are already dealing with a lot to prove and to open up about these issues with people they don’t even know, so that their kid can have an opportunity that they deserve. What if parents don’t even speak English or what if they’re undocumented and don’t have tax documents proving they are of low income?

This is probably related to gender diversity, but you wrote in your pre-interview that you think men should lean out.

Before I joined tech, the concept of “leaning in” surfaced onto my radar. Initially, it felt like this was being proposed as a new idea, something that’s rarely been done before. It frustrated me. I’ve spent most of my life leaning in for survival. And leaning in is simply what marginalized women across the nation have been doing for their basic human rights for decades.

“Before I joined tech, the concept of “leaning in” surfaced onto my radar. Initially, it felt like this was being proposed as a new idea, something that’s rarely been done before. It frustrated me. I’ve spent most of my life leaning in for survival. And leaning in is simply what marginalized women across the nation have been doing for their basic human rights for decades.”

And when I look at the core issue, it’s equity in the workforce. Women aren’t paid fairly, but women didn’t create the unfair ways in which women are compensated. And women of color make significantly less than white women, and face higher rates of discrimination at work. Women leaning in can help change the ways in which women are perceived and treated, but men leaning out create genuine opportunities for women to rise. Leaning out as a man can mean giving up your spot on an all male panel to offer a woman on your team the opportunity, or giving press ops to women, being vocal about the important roles women hold in the company, and of course, paying them a fair and equitable salary. Because the burden of making the workforce fair and equitable shouldn’t be ours to carry.

“Leaning out as a man can mean giving up your spot on an all male panel to offer a woman on your team the opportunity, or giving press ops to women, being vocal about the important roles women hold in the company, and of course, paying them a fair and equitable salary. Because the burden of making the workforce fair and equitable shouldn’t be ours to carry.”

What advice would you have for those of similar backgrounds hoping to get into tech?

We’re all facing different obstacles or adversities, and there are periods in our lives where we may feel like we can’t do what we want. And when we live in a negative environment, you’re not just internally facing challenges, but you’re getting that external negative validation. Whether you are a teen mom or a young person facing any of the many obstacles that make our lives unnecessarily harder than it needs to be, stay focused on your own dreams. Find a mentor or two who are smart and kind, and only trust them for advice and guidance.

And constantly work on yourself and making you the best version you can be. We like to believe that at some point in our lives we reach our full potential, but what if it’s a life long journey where we’re constantly learning and constantly changing and improving? Don’t feel like you have to be the final version of you at this very moment, just be willing to learn. Stay true to who you are and accept that you are a work in progress.

“Don’t feel like you have to be the final version of you at this very moment, just be willing to learn. Stay true to who you are and accept that you are a work in progress.”

I grew up in a multicultural working class community, consisting mostly of immigrant families, right outside of Boston, Massachusetts. It wasn’t the safest or nicest neighborhood, but for my parents it was a step up from the situation back home on the Cape Verde Islands.

“I love it when people tell me I can’t do something and then proving them wrong. I get a kick out of that.”


After the birth of my youngest brother, my mother made two key decisions that would significantly impact our lives and futures. First, she decided to move her family from a troubled neighborhood in Boston to a much safer community. And second; she sent us to a private Catholic school in said community. These events limited our exposure to drugs and gang violence, and got us access to quality education.

My high school was funded by the Bill & Melinda Gates Foundation to supports its innovative model where students would attend regular classes for four days. The fifth day was reserved for a full time job shared amongst five students. We learned valuable, real life skills and could put away the earnings towards our tuition. This is where I was exposed to technology for the first time. I worked with engineers and was quickly captivated by all its potential.

“One of my biggest insecurities is language. English is not my first language, and because of that, I don’t feel like I have the vocabulary to be as persuasive as I’d like to be. Immigrant parents combined with marginalized, low-quality education doesn’t really build a ton self-confidence.
”

Despite the proximity of universities like Harvard, MIT, and Tufts to my home, I never really thought about college until my cousin invited me to spend a weekend with her at Boston College. That experience was transformative for me because suddenly college felt like an obtainable goal. If my cousin could make it, so could I.

My college experience was, like it is for many people who look like me, very challenging. I had to balance lectures and exams with jobs, but that’s how I ended up working for Karmaloop. And at Karmaloop I got exposed to design, art, streetwear brands, marketing – brands like Supreme and Married to the Mob – all of which had strong foundations in graphic design. After I got my degree in neuroscience, I decided to do something for myself. I bought a one way ticket to San Francisco and left everything behind. In San Francisco I found design, technology, art, and myself.

For the first three years I worked as a user research lead for a startup that allowed me to travel all over the world. I got exposed to the long hours and high pressure of tech, but was able to tap deeply into my passion for design.

I worked in tech as interaction designer for a few years now. Those years gave me enough insights into the treatment of women. But one of my biggest issues with the whole diversity conversation is that is it’s often too much conversation. As a designer, I wanted to build and test something that could actually be shipped.

“I fondly remember Ben Horowitz telling me, ‘There’s offense, and there’s defense. And what you’re telling me right now is that you’re taking people of color, who are naturally creative. People of color invented hip-hop, jazz, blues, and rock ‘n’ roll, and you’re putting them in an arena where they’re positioned to win. I think it’s a great idea. Let’s go tell Kanye about it.'”

I quit my job in early 2015 and founded Front & Center. I wanted to expose creative young adults from underrepresented communities to non-engineering roles in tech. I researched and worked with design leaders from Facebook, Google, KPCB, Vice and many others to define a basic set of required skills for product designers that don’t pursue a traditional academic path. That research resulted in a design training program consisting of basic design, communication and presentation skills. Today, I mostly mentor through Front & Center, consult as a designer.



What has your experience been building Front & Center?

I’m very lucky because my partner has been an entrepreneur for years; he helped me out by coaching me on how to avoid typical first time founder mistakes. But even with his help, there is a lot of falling on my face. I saw a problem, but had no solution. So I started building what I thought was right, but while speaking with investors I figured out it’s very hard to find a model for something that usually fits within the non-profit mold. So I had to do a lot of catching up on how to run an actual business, so I wouldn’t look like a fool. And one of my biggest insecurities is language. English is not my first language, and because of that, I don’t feel like I have the vocabulary to be as persuasive as I’d like to be. Immigrant parents combined with marginalized, low-quality education doesn’t really build a ton self-confidence.


“You know when they say, ‘just fake it till you make it,’ right? Well–it’s super hard for me to fake anything because I have no reference points. Getting help from someone that’s gone through similar hurdles is practically impossible because there are very few people who look like me that do what I do. Finding people you can look up to and model your progress after is so important to individual development. Even today I struggle to find role models. There are very few successful black women who made it as designers.”

I’ve been able to expand my network with some amazing people. I fondly remember Ben Horowitz telling me, “There’s offense, and there’s defense. And what you’re telling me right now is that you’re taking people of color, who are naturally creative. People of color invented hip-hop, jazz, blues, and rock ‘n’ roll, and you’re putting them in an arena where they’re positioned to win. I think it’s a great idea. Let’s go tell Kanye about it.” Now these kinds of things happen in Silicon Valley, but all I could think of was “Oh my god, I get to meet Kanye West.” Moments like these don’t come often when you’re a founder. They definitely don’t come when you’re a founder from a marginalized community. But moments like these keep you going, wherever you’re from as a founder.

Tell me more about just the struggles you’ve overall had in your time of tech. What are the roadblocks you’ve had to overcome?

You know when they say, “just fake it till you make it”, right? Well – it’s super hard for me to fake anything because I have no reference points. Getting help from someone that’s gone through similar hurdles is practically impossible because there are very few people who look like me that do what I do. Finding people you can look up to and model your progress after is so important to individual development. Even today I struggle to find role models. There are very few successful black women who made it as designers. So you have to look beyond your appearance, One person that has inspired my way of thinking about the world is Elle Luna. She’s a person that lives her truth, and I’m thankful to have learned that it’s enough to be inspired. Having role models that look like you is great. But when there aren’t any out there, you need to learn to look up to individuals that don’t necessarily look like you.


I can’t stress enough how important role models are. And I want to be that role model for the community that I’m from. When I hear celebrities say, “I’m not a role model, I’m an artist, I can do whatever I want”, I say no: You’re one of the few that made it out. You can show others how to do that. Passing on information is so important to break the cycles of division and separation. I’m in a unique position to set the example for future generations.   


I’ve been thinking a lot about tech-debt in communities of color lately. Access to technology in communities like the one I’m from is incomparable to the access to technology that most people who become successful in Silicon Valley have. Most Black schools have pretty abysmal computer science labs. Students don’t have computers at home, let alone an internet connection. So next to figuring out what stock options mean, a lot of people who are trying to break into technology need to catch up on people who’ve been exposed to tech for much, much longer. I had the privilege to get my first personal computer when I was 14 years old. And I didn’t really know what code was until I was 19. But most of my peers in tech have had access to technology for all their lives, and role models that encouraged them to explore. For people who come from communities like mine, a career in tech is like a pipe dream. There is nobody around you who’s made it in tech, and no parents of family members who can tell you about the career opportunities. Sure, leadership skills come somewhat naturally, but communication can be a challenge when you haven’t been exposed to tech culture like so many of the people around me have.

“I’ve been thinking a lot about tech-debt in communities of color lately. Access to technology in communities like the one I’m from is incomparable to the access to technology that most people who become successful in Silicon Valley have. Most Black schools have pretty abysmal computer science labs. Students don’t have computers at home, let alone an internet connection. So next to figuring out what stock options mean, a lot of people who are trying to break into technology need to catch up on people who’ve been exposed to tech for much, much longer.”

How do you think your background in behavioral science helps you in your work? Both as a product designer and as an entrepreneur.

Having an academic background has mostly triggered a thirst to keep learning. I like watching things and studying their patterns, which is another side to this inclusion discussion that I find remarkable. When people stop learning and stop questioning the way the world works around them, things like bias, discrimination and racism come into play. I’ve been trying to fix that conversation by prototyping solutions that can actually be implemented, and found that in order to work in tech – an academic path is very beneficial but in most cases, not an absolute necessity. Especially in the field of design.

What would you say are your big motivators?

I love it when people tell me I can’t do something and then proving them wrong. I get a kick out of that. I decided to speak out more because I want kids to know how to deal with similar situations. I want them to say, “I want to be like Melanie when I grow up.” I didn’t have anyone I could be like growing up. So I collected all this advice; some of it I can use, some of it I can’t. Bits and pieces of people that have inspired me along the way, and I try to keep improving myself like that.

Okay, let’s just go macro real quick. How do you feel about the state of tech in 2016? What excites you, what frustrates you, and what would you like to see change?

I’m most excited about  companies that exist to do good and challenge the way we think about the world, so I’m really in love with Honor. I love what they’re doing, I love the problem that they’re solving. It’s really exciting because it’s a human problem and everyone benefits from it. The workforce, the families, even the way they run the company.


The things that frustrate me? There are still too many non-problems being solved. Things that are only accessible by a very controlled, homogenous audience. I’m worried about the accessibility of technology. Many processes continue to optimize and drive down prices, making things more affordable – but there very few processes that focus on making life more enjoyable.

What advice would you have for folks coming from similar backgrounds as yours who are hoping to get into tech?

You need that hustle. A strong will to succeed because you will hear “no” more often than people will tell you “yes.” Shit will get hard. But if it’d be easy, anybody would be doing it. We experience racism and other difficulties every single day. Use that sadness and anger to lift yourself up in the right direction. If people don’t believe you, build whatever you can and try to prove them wrong. With Front & Center I’ve tried to hack a system that I found didn’t make sense. So I decided to make a change. I measure my success by the opportunities I create for other people. I want people to join me in designing a more inclusive future.

“You need that hustle. A strong will to succeed because you will hear “no” more often than people will tell you ‘yes.’ Shit will get hard. But if it’d be easy, anybody would be doing it. We experience racism and other difficulties every single day. Use that sadness and anger to lift yourself up in the right direction. If people don’t believe you, build whatever you can and try to prove them wrong.”

I was born in New York. My mom and dad lived in a bad neighborhood and then I think my dad caught someone pulling a TV, their TV out of their apartment at one point, and then they decided to move to the suburbs.

The suburbs are what? Only 30 miles away from where they were in New York, but it’s a world apart. It’s really the kind of place where someone like me can grow up, and just not quite fit in. I think that was really important to my development, because it got me really used to thinking for myself. That’s been really the most satisfying thirty-something-year arc in my life going from public schools in New Jersey, all the way to corporate publishing jobs to doing my own things that are weird and special in their own way and loved for that. That’s been a really big trend in my life, just that feeling of not quite agreeing with the crowd. I started understanding that in New Jersey.

“That’s been a really big trend in my life, just that feeling of not quite agreeing with the crowd.”

What was it like? You are first-generation American on both sides, right?

I think I’m one-and-a-half. My mom has a really thick Queens accent. She went to fashion school in New York she designed jeans in the ’80s for Jordache. My dad is from Hong Kong and was a computer engineer for Hewlett Packard in the ’80s.

What did your parents expect of you growing up? What did they think you were going to do?

My parents really didn’t expect anything, and that was maddening at times. When you’re a kid, you get put into music lessons. I was like, “I don’t want to do this,” and they’re like, “Okay.” That’s not a normal reaction for stereotypical Chinese parents. They were letting us do whatever we wanted to. It’s reflected in the professions of all my brothers. One of my brothers is a musician. Another brother is a furniture maker. That has led to us having not a ton of guidance or structure.

My dad had a really overbearing dad and overbearing older brother, so he never wanted to tell us what to do, as a matter of principle. My mom was just really into being a free spirit. She let us do our own thing. To be honest, when I was younger, that really came off as not giving us enough support, direction. I don’t think people become really, really excellent without some sort of pressure, and that was kind of the pressure that I was given. It wasn’t ever pressure to get good grades. It wasn’t pressure to be a doctor. It wasn’t pressure to do anything and except be myself and do what I wanted to do. It’s a lot of responsibility to listen to what yourself and find out what’s right for you, without anyone programming you for that.

“It’s a lot of responsibility to listen to what yourself and find out what’s right for you, without anyone programming you for that.”

You mentioned that going to school in New Jersey was weird. Tell me more.

I think it was like subtly racist in a way that it just is. In a way that’s not explicit, and I think there’s a weird social dynamic there. That’s part of why I moved to Hawaii. It’s like I don’t need to be a minority anymore. And I really carry that confidence with me that I get from living in a place where I’m not a minority, all the time. New Jersey was just kind of very racist, very classist. It was just like not where I belonged. I’m into deep urban-ness, or I’m into nature, but I’m not into this gray mushy zone in between, that’s kind of what the suburbs were for me.

What were your inclinations as a kid? Did they skew technological? Did they skew towards writing?

My father was an engineer, and we didn’t play sports. We would build remote-controlled cars, and I built my first by myself at 7, and the 16-year-old guy across the street couldn’t figure out how to build his, so I knew I was kind of a nerd by that time. We played around computers, and went shopping for gadgets in Hong Kong during my summers. I just had an aptitude for writing and reading when I was younger. I think, I’m actually at the same reading a comprehension level, now that I did when I was seven. Can you imagine not being any better reading when you’re 39 than when you were seven years old? It’s like bizarre.

Tiny genius Brian.

I don’t know if genius is the thing. It’s like, “why haven’t you got any smarter since you were seven?”

I like the bird sounds that are happening on that side of the audio.

That’s funny that you can hear that. There’s parrots here. I think they filmed some Elvis movie that had green parrots, and then they released them at the end of the filming and then they started breeding. It’s this weird invasive, beautiful parrot species that lives in my neighborhood.

Walk me through the windy path that got you into tech, and your editorial career in tech.

I don’t even know—I don’t consider myself in tech. I went to college in Boston and I switched majors about six times, and I took summer school every summer to catch up, but I never did, and ended up with—you needed 100 credits to graduate and I had 150 by the time I was done. I went from Philosophy to English to Journalism to Photojournalism to Computer Science to Business with an IT slant on it. I was pretty good at photojournalism and really fast in the dark room. Then one day this journalist comes in from the Boston Globe and this was like 1999, so it was beginning of a pretty dark age for newspapers. They could see the internet coming. This one veteran was like, “80% of you won’t get jobs and 20% of you who will will work 80 hours a week for $20,000 a year. It’s going to be bad.” And the same week this artist woman that I was madly in love with said, “Well, I want to be an artist, so I’m probably going to have to marry someone who’s financially responsible.” And I was like, “Alright, maybe I should go to business school.” So I transferred because I was a pretty reckless, idiotic, romantic young person.

I didn’t like it at all in business school. I didn’t fit in. I didn’t have nice clothes. And I didn’t do great. But then it was like 2000, and I got a job at this small web-development firm, and within two months of getting that job I got laid off from the bubble bursting. There were no jobs. So in San Francisco I remember, like, seven people who were let go were crying and then I was just like, “Thanks for the job, it was really nice meeting you.” I just kind of knew that I wasn’t supposed to be doing that kind of work. Plus a couple times I got in trouble for reading about gadgets online, I don’t know why, but it was just interesting foreshadowing.

“I didn’t like it at all in business school. I didn’t fit in. I didn’t have nice clothes. And I didn’t do great.”

I went to work at my boxing gym at the time that I’d just joined. I’d always had a really strong affinity for martial arts. I joined this gym, and I went from answering phones and signing people up and sweeping the floors to eventually teaching. That took like 3 or 4 years and I think I learned a lot in that gym about hustle and working hard. I was so happy, just sweeping the floors and exercising like 5 hours a day, 6 days a week and getting into really good shape, making like 5 or 6 dollars and hour. My life was really simple. At one point, I started to just notice like, philosophically, I was not that aligned with this concept of fighting all the time.

I remember fighting with this woman who became a professional later, she punched me in the nose, and then she was like, “Do you want a tampon?,” it was like the constant joke, my nose used to bleed all the time. So, I just started to realize people in the gym were kind of crazy in a way that I didn’t necessarily want to be. Also, fighters don’t age well, they get beaten-up, and you get brain damage, and they start slurring their speech and it’s just really rough. I saw the writing on the wall, but at some point it really came together when the owner of the gym was hurt as badly as can be.

“I went to work at my boxing gym at the time that I’d just joined. I’d always had a really strong affinity for martial arts. I joined this gym, and I went from answering phones and signing people up and sweeping the floors to eventually teaching. That took like 3 or 4 years and I think I learned a lot in that gym about hustle and working hard. I was so happy, just sweeping the floors and exercising like 5 hours a day, 6 days a week and getting into really good shape, making like 5 or 6 dollars and hour. My life was really simple.”

We would practice in a warehouse space and it had a garage door so we could get airflow. The professionals, who trained in the afternoon, were practicing when all a sudden we hear this crash. Out in front, some guy in this like Jeep Cherokee—he looked like a total techie yuppie, some redheaded nerdy dude—had taken his green Jeep and backed it into a car that happened to belong to the owner of the gym, Alex Gong. He was a professional fighter. I think his fight name was F-14, as in the jet.

The techie put his car in drive and took off down Clementina Street into 5th. Alex being Alex, super combative, professional fighter, super aggressive dude, chases after him wearing boxing shorts and no shirt. I think he took off his boxing gloves, I don’t know. Chases him down. The guy gets stuck in traffic on 5th by the highway entrance. I chase after him with a camera because I’m like, “Well, I’m starting to be a journalist. Let me take a photo of the license plate.” So I run a block, I catch up and I see Alex reaching into the car and getting the guy to try to pull over by taking his keys out. The light turns green, and I hear, “Pop,” and I see Alex fall down. Alex was shot in the chest by this totally yuppie looking guy. The guy took off. Some witnesses got the license plate. A cop showed up immediately, but Alex was dead on the ground.

I don’t remember what I did. Somehow I told the people at the gym that Alex had gotten shot. I don’t know if I had a cellphone back then. Alex was lying in the middle of the street, wearing boxing shorts and I was the only one there who knew him. The cop said, “You should give him CPR.” I’m like “He’s got blood and vomit all over his mouth.” He’s like “use your t-shirt as a mask” So I used my t-shirt and I gave him CPR but in my head, I’m like, “He’s so dead, there’s not even any blood coming out of his wound on his chest.” I just knew he was dead. There was no reviving him. He was shot around the chest, around the heart.

For me, the entire situation can be summed up as live by the sword, die by the sword. So we grieved, and nobody really took the lesson the way that I did. And my lesson was you have to find a way that’s not as conflict-oriented in life.

From then I just really started putting energy into my work life. I took the tools from the gym, the work ethic, the hustle, the pacing, the style, the strategy and I put it towards work. I would just work so hard and I got whatever job I wanted eventually, even if I had to apply a few times. That’s how I got in the door at Wired Magazine.

“From then I just really started putting energy into my work life. I took the tools from the gym, the work ethic, the hustle, the pacing, the style, the strategy and I put it towards work. I would just work so hard and I got whatever job I wanted eventually, even if I had to apply a few times. That’s how I got in the door at Wired Magazine.”

I spent a few years there, but it was like me and sixteen senior editors who never really listened to me, as was their right. That’s just how it was at magazines. And so I left for Gawker where I got a job running Gizmodo, which at the time was small. You didn’t leave a magazine for a blog in 2006, it wasn’t a thing yet. But I knew it was a place where I could do my own thing. And so that’s how I got into being editor-in-chief at Gizmodo. And for five years it was not that different from boxing; being punched in the face every day was actually easier than working at Gawker. It was like so combative internally, so combative externally and you burn all these bridges and you just piss everyone off. But you’re doing that to get the story and get it fast. And I really liked that, but I really liked helping people more, which is what led me to leave and do Wirecutter.

It’s funny, this fall I’ll be at Wirecutter five years, and that’s how long I was at Gawker. But at Gawker, I was thirty-five pounds heavier than I am now, because I was so unhealthy, and so unhappy, and so stressed all the time. So, it’s kind of like I can feel my life evolving in a way that I really like.

“And so that’s how I got into being editor-in-chief at Gizmodo. And for five years it was not that different from boxing; being punched in the face every day was actually easier than working at Gawker. It was like so combative internally, so combative externally and you burn all these bridges and you just piss everyone off. But you’re doing that to get the story and get it fast. And I really liked that, but I really liked helping people more, which is what led me to leave and do Wirecutter.”

What was the impetus for starting the Wirecutter?

I always thought it was really weird when I’d talk to other people who are not into tech, they would ask me, “What do you do?” And I’d go “Oh, I run one of the biggest tech blogs in the world.” But the weird thing is if they weren’t in the tech industry, they’d always ask me this one question, which is, “Oh, I’m trying to buy this, like, camera or this TV, or headphones, or—which thing has thing has this, or—can you help me?” And I’d be like, “Actually, I don’t know.” Like I don’t know. Like I know about all these news things, but you just don’t write about that what people should actually buy.

I just saw this opportunity for this list that was not going to make a lot of traffic, but it would just be this master list of, hey, if you need, like, a $500 TV, this is the one you should get. It sounds like, to some people I describe it to, they’re like, “That sounds like what already exists.” And I’d go, “Yeah, but what already exists will take you, like, an hour to sort through, whereas we only need two minutes to use this list, The Wirecutter. Do you want to save 95% of your time that you spend comparison shopping on this one article that can just help you instantly?” And the answer is yes, and once people use it, they get it.

After leaving Gawker, I had all these really great job offers, but I really wanted to do The Wirecutter. I couldn’t stand the thought of it not existing. So I started out small. I just Airbnb’d my house, and sold my fancy car and just got a cheap truck, and I just started working on it. At some point, the idea just popped. I was just living in Hawaii trying to balance out work and surf, and just everything started to get super amazing. I only expected to do it as a hobby, but it became a real obsession for me.

“After leaving Gawker, I had all these really great job offers, but I really wanted to do The Wirecutter. I couldn’t stand the thought of it not existing. So I started out small. I just Airbnb’d my house, and sold my fancy car and just got a cheap truck, and I just started working on it.”

How did all your time in the blogosphere and the whole tech ecosystem affect your decision-making strategy as an entrepreneur?

I have a lot of disadvantages compared to normal CEO. I think as a journalist you have a lot of common sense and you have a good nose for bullshit, and you need to do stuff that you believe in. The Wirecutter was a concept I could really believe in, but I also knew that, because it was so kind of radical at the time, people were like, “How are you going to be ranked on Google? How are you going to make traffic so you can make ad money?” My pitch was like we are going to ignore a lot of noise and only be updated 10 times a month at most. They’re like, “You’re only going to do 10 articles a month?” I’m like, “Yeah.” Then they’re like, “I don’t know how that’s going to work money-wise.” I’m like, “Neither do I. I’m not sure. I don’t care.” If you’re a VC, you’re probably not going to understand why you should give me money after a conversation like that.

“My pitch was like we are going to ignore a lot of noise and only be updated 10 times a month at most. They’re like, ‘You’re only going to do 10 articles a month?’ I’m like, ‘Yeah.’ Then they’re like, ‘I don’t know how that’s going to work money-wise.” I’m like, “Neither do I. I’m not sure. I don’t care.’ If you’re a VC, you’re probably not going to understand why you should give me money after a conversation like that.”

We got a launch sponsor, Intel, but I don’t think anyone but me understood that we were going to have so little traffic because we were not publishing junk en masse. God bless them. I just also knew that in publishing, you can’t apply those kind of models of extreme growth that you can get from launching a free app that has a free service that grows so fast because it’s all free. You know, like you can’t match that with content. Content’s pretty expensive. Anyone who says it’s not is doing garbage. It just doesn’t grow the same way, and if it does it’s growing because of kind of tricks. So, to do something that’s really high quality, you need to allow it to grow very slow in a way that’s not compatible with most modern, tech-oriented VC, and that’s basically what we’ve done. It took about 2 years before I really could pay myself outside of poverty levels but I didn’t need much. I just kept borrowing money and just living very frugally and I just didn’t want anyone telling me what to do or to do it faster. I think that way was the key.

“Content’s pretty expensive. Anyone who says it’s not is doing garbage. It just doesn’t grow the same way, and if it does it’s growing because of kind of tricks. So, to do something that’s really high quality, you need to allow it to grow very slow in a way that’s not compatible with most modern, tech-oriented VC, and that’s basically what we’ve done. It took about 2 years before I really could pay myself outside of poverty levels but I didn’t need much. I just kept borrowing money and just living very frugally and I just didn’t want anyone telling me what to do or to do it faster. I think that way was the key.”

What metrics have become most important to you?

Metrics? Any two solid metrics that kind of go against each other really work for me.

Sessions is really cool because it rewards my team for not only getting new people but having people return. Having people return is a sign of quality and satisfaction and that’s what we’re going for. On top of that, we’re doing some interesting stuff with data. We ask questions like, “Do you need an 8,000-word article on 10-dollar vegetable peelers?” We’ve also learned that after people trust our work, they only read the first like 30 seconds, and then they stop, and they buy what we recommend.

“After people trust our work, they only read the first like 30 seconds, and then they stop, and they buy what we recommend.”

How many people are you paying regularly now?

Roughly 60, plus freelancers. Sometimes people just think it’s me doing it by myself!

What do you think are the biggest motivators behind your work?

The Wirecutter is a really mission-oriented place. So we are not here to make traffic, or be a big media company, or be fancy. We’re just trying to be really useful for people. Shopping really sucks. Everyone has a couple things we’re really excited to shop for, whether that’s leather jackets or surfboards or something that you just will spend unlimited amount of time shopping for. But most stuff’s not like that. Shopping really sucks. It’s such a waste of time and it’s stressful and why even bother with stuff that you’re not that excited about? Helping people with those situations gets us up in the morning. When someone’s like, “Oh, I don’t know what to get. I hate this,” and I can drop a Wirecutter link in front of them like, “Here you go.” That is the most satisfying thing. I love that feeling.

I’m currently using three different things I brought on The Wirecutter for this project.

A microphone?

A little lav and a little recorder and my monitor.

Awesome.

What personally motivates you to do all this stuff?

I think it’s really complex. I love my work so much. I’m satisfied in that regard. But, I would say that, it’s also at the end of the day, we are not our jobs. I have so many things I love to do. I just wish there were 48 hours in a day. Right now, I’d say work takes up 80% of my energy, maybe 90%. I think that’s normal in most people, especially San Francisco friends who work very hard. But that’s not really how it is in Hawaii for a lot of my friends.

You mentioned that in Hawaii, you are not a minority anymore and that is something that you appreciate. I’m curious to know if you experienced isolation or otherness in Silicon Valley?

I think in San Francisco and in tech, I think like being an Asian male is probably the same as being a white male. There is not a ceiling there, or it’s a reduced ceiling. Maybe it’s not on the executive level where you still don’t have a lot of diversity. But San Francisco’s not bad. I think socially, I think in dating there’s discrimination. The data scientist from OK Cupid wrote a book and paraphrasing his findings, he said, “people are really racist when it comes to dating.” The feeling of discrimination is not as strong for me in places where I am not a minority, like in Hong Kong or Hawaii.

Do you have any advice for folks hoping to make it in the big world of tech?

I think you have to take some things really seriously, and then some things not seriously, and you just have to have the wisdom to know the difference. There’s knowing how to work with others, but not following people blindly. There’s a lot of seemingly contradictory advice that isn’t really contradictory if you understand the nuance. Anyone who’s really doing well, in any field, has a bunch of similar traits and mindset. They have these seemingly contradictory things in balance where they do know how to work in a group, but they also are not beholden to groupthink.

What I realized about my friends in San Francisco and LA is that people in California are so much more brave, optimistic, willing to just go for it, than my friends in either Hawaii or New York. I really appreciate that about California, and San Francisco in particular. Everyone is just trying to do pretty big things, if not huge things. That energy is contagious. It’s beautiful to have this example of a peer group that is not afraid to go for it.

“I think you have to take some things really seriously, and then some things not seriously, and you just have to have the wisdom to know the difference.”

I was born in Seattle, but my dad was in the navy so we moved around a bit. When I was 8, we moved to the Philippines where I lived for 15 years, so I pretty much grew up there.

What was it like growing up there? Especially as someone who had a taste of the States.

It was difficult at first because I didn’t speak Filipino, so I had a tutor to learn it. It was weird at first because obviously I look Filipino, but other kids treated me differently because I didn’t speak the language and I sounded different.  But I was young so I adjusted quickly. I started college when I was 16 and majored in Computer Science.  The plan was always to come back to U.S after we graduate, but I had a little detour. 

In my senior year, I had an unplanned pregnancy. It was really difficult being in a Catholic university in a conservative and predominantly-Catholic country.  I felt like I disappointed my parents and was a cause of embarrassment in the family.  I was a good kid, I had good grades and a good life, I just made a bad decision.  I was fortunate that my mom really pushed for me to finish college.  A lot of other girls in the same situation would have dropped out of school because the family wouldn’t be able to face that embarrassment. I got married then a few months later I had my daughter.

“In my senior year, I had an unplanned pregnancy. It was really difficult being in a Catholic university in a conservative and predominantly-Catholic country.  I felt like I disappointed my parents and was a cause of embarrassment in the family.  I was a good kid, I had good grades and a good life, I just made a bad decision.”

I had to postpone a final project presentation because she arrived 2 weeks early.    Because I was busy with my senior year, I didn’t have time to attend childbirth classes or read books.  I didn’t even know an epidural existed until years later!  A week after giving birth, I had to go back to school for final exams. I wasn’t planning on attending graduation but I found out that I graduated cum laude and actually 3rd in my class. My parents attended and they were happy and proud of me.

After graduation, my husband and I each moved back with our parents. My parents offered to look after my daughter so I could work.  My mom was a stay-at-home mom and didn’t get to use her Engineering degree and she said “I want you to have a career.”  But in the small hometown where we lived, there were no software jobs.  This was back in 1999 and unless you lived in Manila, there wasn’t much to do with a CS degree.  

Not that I had the time or energy to really think about my career. I was pretty much in survival mode and all I needed was a job so i can feed my baby. I got a job teaching at a small technical college and after a semester, I worked for another company but didn’t really use much related to CS.  My husband and I split up in the meantime.  It was a lot of stress for a young marriage.  

What did you do to try to turn things around?

After my daughter turned 2, I decided it was time to come back to the US to find a better job.  My sister was kind enough to lend me money for a one-way ticket to Texas where she and my other sister lived.  The hardest part was leaving my daughter with my parents.  But I had to until I could find a job and be able to afford to support the both of us.  It was pretty scary. It was 2001 during a recession and it was hard to find a job.  I had a few temp jobs doing random things, like sorting mail and data entry.  Finally, a small software company hired me to do customer service. I was able to save some money, and after 7 months of being apart, my parents brought my daughter here. I stayed at that company for 7 years, and I went from customer service to QA.  In the middle of this, I remarried then after 3 years got divorced to get out of an unhealthy relationship.  On top of that I had $24,000 in debt.  I really made all my stupid decisions in my 20s. 

“After my daughter turned 2, I decided it was time to come back to the US to find a better job.  My sister was kind enough to lend me money for a one-way ticket to Texas where she and my other sister lived.  The hardest part was leaving my daughter with my parents.  But I had to until I could find a job and be able to afford to support the both of us.”

I then moved to a big semiconductor company where I stayed for 4 years. My life started stabilizing in my 30s.  It took me 2 years to get completely get out of debt.  I was making better money.  And I was in a healthy relationship.  After Thanksgiving in 2012, most of our business unit got laid off. It was my first time to experience this. It was scary especially being in a single income household.  

All these years I was in a career crisis. I didn’t really know what I wanted to be when I grow up [chuckle]. I always hear “follow your passion” but this was never clear to me.  I have a lot of things I’m interested in but none that I’m both passionate about and am good enough at to make a living.  If I had followed that advice, I’d probably be a failed travel blogger. So back to getting laid off.  Part of our package was tuition reimbursement. The idea was for the company to pay for you to acquire some skill to get a new job. It wasn’t enough money to get a new degree and believe it or not, I used to dream up my ideal job and think, if only I studied to become a lawyer or an accountant! In the end, I thought, okay, practically speaking, with this amount, what can I do?  Well, I have a CS degree and I haven’t written a single line of code since I graduated so maybe I should learn a new language.  I searched for the top jobs in my field.  I looked at jobs at Google, Amazon, and Apple, and I was just curious, what kind of skills are they looking for?  Long story short, I signed up for an online Python class.   It was difficult at first to get started, but I realized that the concepts that I knew were the same, just the syntax was different.  It was like falling in love again!  It was exciting solving each problem, the same feeling I had solving problems in BASIC when I was 9, and Pascal in college.

In the meantime, Amazon had contacted me and many of my co-workers through LinkedIn because a lot of the skills we had in embedded software were what they were looking for.  I went for the interview thinking, “This is really going to be a practice interview. There’s no way I’m moving to California.” [chuckle].  I got a job offer, and it was compelling enough for me to consider it. It was a hard decision to leave my support system, and move to a place that I’ve never been to before where the cost of living is just so high.  

The move turned out to be the best thing that happened to my career!  I continued learning Python and applying it at work.  I found that the better I got, the more I felt enjoyment and passion in my work. The move also turned out to be great for my daughter, being able to play in one of the top high school drum lines in the US. She cried at first because she would be leaving friends and going to a new high school.  But she said, “If you think that’s what best for us, then I will support you.”  

Like a little adult.

Yeah. I think because it’s just the two of us, I tend to talk with her about everything, including finances. So she understood why we made the move.  Anyway, I feel like I have so much energy and desire to learn new things.  Next year she’ll be off to college so I’ll even have more time to focus and go on to the next phase of my career.

What a story. What overall is the most exciting to you about working in tech? What things are you really proud of and what about the work really activates you?

What I love about working in tech is being able to work on products that change people’s lives.  I read the reviews on Amazon Echo and it’s amazing to see how customers use device, especially disabled people.  It’s pretty exciting and inspiring.

People are speculating that technology like the Echo is the future.

Yes it’s very exciting to be part of that!

I’m curious to know what it was like culturally going from the Philippines to Texas, then from Texas to Silicon Valley.

Culturally, going from the Philippines to Texas was a breath of fresh air for me.  In the Philippines there was such a stigma of being a single parent.  You and your child get either judged or pitied on.  Hopefully things have changed there since then.  Regarding moving from Dallas to the Bay Area, I love the culture of learning and trying to be the best at what you do.  There are so many movements, organizations, meet ups in tech that it’s not hard for the enthusiasm to rub off on you.  I’m not saying it didn’t exist in Dallas, but maybe I just was not in that environment.

What has your experience been work-wise as a single mother?

The biggest difference for me is not being able to travel for business.  It has to be planned and I could only go if I had someone I trusted, like my parents, to look after my child.  I think that being a parent is hard whether you’re a single parent or part of a two-parent household.  As far as my daily work, when my daughter was younger, I had to force myself to be efficient because I didn’t have the luxury of staying extra hours if I didn’t manage my time well.  

What’s it been like, leaving your support network in Texas, and then trying to find support networks here?  Have you found them yet?

It was difficult leaving my family and friends. I’m a bit towards the introverted side, so it took effort and courage to put myself out there and make new friends.  I mentioned that my daughter is in the drum line at her school’s marching band.  Volunteering for that enabled me to meet other parents who were very welcoming.  It definitely involved getting out of my comfort zone.

“I always come across difficult problems to solve at work.  But they’re almost never as bad as the difficult problems I’ve had to face in life.”

Have you had any particular mentors in your career?

Yes, in Texas I had a good manager who mentored me when I was new to QA.  I’ve also had several good managers since I moved here.  One managed me remotely from Seattle and he always talked about improving my skills thinking not just about my current company but for my future career.  I thought that was kind of refreshing. Maybe that was another one of those cultural differences back in Dallas where I didn’t feel like I could be that open with my managers about my career because if it may not line up with what is best for their team.  You have this fear of being the first to go in a layoff if they knew you had any thoughts about leaving.  Here, no one expects you to stay in one place for 10 years, or even 5 years, so you can be much more open.  

It’s like to keep you, they have to nurture that.

Exactly. Having a good manager is important to me, so when I interview, I make sure it goes both ways.  

What do you look for in a job now compared to earlier in your career?

I look for somewhere where I can add value to team or company, in an environment that supports autonomy and creativity. It would be great to work on something that customers love, and I can say, “I worked on that!”  

How do your friends and family feel about how far you’ve come?

My parents were always supportive of me and cheered me on every step forward I made.  Today, I feel that I’ve made my parents proud.   My daughter always thanks me for being a great mom.  That means a lot to me. 

How do you think the combination of your background and all of your life experiences impact the way that you approach your work?

I always come across difficult problems to solve at work.  But they’re almost never as bad as the difficult problems I’ve had to face in life.  I also am not confused anymore about what I want to do with my career.  Getting rid of that lingering doubt helps me focus better.   

Let’s go macro for a second.  How do you feel about the state of tech in 2016?  Like what is exciting to you, what frustrates you?

I think the Connected Home and Internet-of-Things will be big this year.  I’m excited to be part of that.  But I think it will be important for people to distinguish between the ones that improve your quality of life and others that are just innovation for innovation’s sake.  

Technology aside, I see a lot of exciting and frustrating moments about improving diversity in tech.  Women in Tech in particular is close to my heart, having a daughter who is exploring careers and deciding what to major in.  I see a lot of movement around this and I feel hopeful.  She took Java programming this year at school to test the waters and see if she liked it enough to minor in Computer Science.  She had a good experience and now she is thinking about majoring in it.  She might still change mind of course, but my hope is for her to experience a more gender-diverse tech world than I did.  

What are your goals for 2016? Either for work or for yourself.

I have a lot of goals.  At the start of each year, I write my goals for the year  and I like to revisit it throughout the year to see if I’m making progress.  The career goal I set for myself this year was to switch roles from a QA Engineer to a Software Development Engineer in Test.  I talked with my manager about it and I’m happy to say that I am working on that transition now.  My personal goals involve getting better at programming, reading more, traveling more, living healthier, watching more concerts, getting back into playing the drums and maybe even playing in a band!

Where do you see yourself in five or ten years?

I would love to be a software developer and build something.  In 10 years, I’d love to be able to at the top of my industry.  I don’t know what that will look like yet.  Maybe those jobs don’t even exist yet, just like many of the tech jobs now didn’t exist 10 years ago.

My last question for you would be, what advice would you have for folks that are going through some hardships, or had crazy life obstacles thrown at them and are trying to figure out their career?

Have a goal, make a plan and focus on the process of getting there.  There are times when life is crazy that you don’t have the time or energy to even focus on your career.  But it’s not always going to be a hardship.  Set realistic expectations given the situation that you currently have.  For example, when the kids are young and you don’t have help, maybe all you can focus on is raising them and doing “good enough” at your job.  Accept that that’s where you are right now.  They will get more independent as they grow, and you can execute on your plan one little step at a time.  Manage your time well.  We all only have 24 hours in a day.  Figure out what’s important to you.  For me, getting 8 hours of sleep is priority.  If you feel like you never have the time or energy, try to identify and fix the unimportant things that suck up your time, or things that cause you stress.  It might be debt, health, relationship stress.  Read books and learn from other people on how to deal with these problems.  There’s no need to learn all of life’s lessons the hard way.  It makes it easier to work on your career when you can lessen or eliminate other stresses in your life.  Lastly, for parents, don’t let your life revolve around your children.  They will turn 18, graduate and be on their own. Don’t forget to treat yourself with love and kindness.

“Have a goal, make a plan and focus on the process of getting there.  There are times when life is crazy that you don’t have the time or energy to even focus on your career.  But it’s not always going to be a hardship.”

I grew up in the Midwest in a town called Waterloo, Iowa. I lived there my whole life and went to undergrad at The University of Iowa for Mechanical Engineering, then moved out to California to study Systems Engineering at UC Berkeley, where I literally knew one person (hi Scott!). I was only supposed to be here for 9 months—the length of the program—but so far I’ve been here for 9 years…whoops.

Funny how that happens.

Yeah.

I’m curious what it was like being a first generation American in Iowa being raised by immigrant parents.

My parents both left Vietnam in the 70s and started out with almost nothing. As immigrants, they were always kind to others because they were just grateful to be here.

As a native Iowan, I will vouch for the fact that Midwesterners are very nice people.

Naturally, when you combine that Midwestern niceness with being an immigrant, you get some extra nice folks.

So interesting. You’re first generation college too. Did you parents expect you to go to college?

Both of my parents sacrificed so much for my brother and I to go to college that it seemed like a shame not to go. Their expectations were pretty strict, both in and out of school, but any struggles I had always seemed to pale in comparison to to theirs. So what if I had homework? At least I was fortunate enough to go to school.

Walk me through your time at Berkeley, and then eventually getting into tech. Did you know you would end up in tech?

Spring of 2008 was a pretty shitty time to graduate, regardless of most degrees. The economy was so bad that 1 out of 4 of people my age was unemployed, and I was one of them.

Getting a job seemed like a bit of a pipe dream, so I moved in with my aunt in San Jose. There wasn’t any Wi-Fi at the house, so I would walk a mile every day to Barnes and Noble in the mall to look for and apply to jobs. I think I ate at every single place in the food court during that time, haha.

I applied to over 250 jobs, had a couple dozen interviews, and did a bunch of odd jobs like data entry, event promotion, and tutoring to get by. At the time, my monthly budget was $600 for rent, food, and everything else.

For a year and a half, even with two engineering degrees from well-regarded universities, I didn’t receive a single job offer.

My lucky break came when my friend’s mom wanted a new brand for her law firm. Her son connected us and I started by designing her a logo. She liked my work and we enjoyed working together so much that I ended up rebranding her website as well, based on the new logo. Her site was the first I had ever designed and built. On top of that, we developed a friendship that continues to this day.

Awesome. So walk me through the experience of getting into tech. What happened after that first website was built, and how was that experience for you?

While I was working on that first website, people I met at networking events or just any casual parties would ask what I was doing, so I would say “I’m working on building a website.” A lot of people responded with “Oh that’s cool, I know someone who needs a website” or wanted one for themselves, so I got more and more clients just by word of mouth.

Through a friend, I found a job with a web consulting firm in San Francisco, but around the same time I started working for them part time, I also received a full time job offer at Lawrence Berkeley National Lab.

“I applied to over 250 jobs, had a couple dozen interviews, and did a bunch of odd jobs like data entry, event promotion, and tutoring to get by. At the time, my monthly budget was $600 for rent, food, and everything else. For a year and a half, even with two engineering degrees from well-regarded universities, I didn’t receive a single job offer.”

I worked the two jobs in parallel but my heart was really in web design and development, so I decided to quit the energy research job at Lawrence Berkeley and focus on what I loved doing. I remember thinking: “Am I crazy? It took me a year and a half to find a job, and now I’m leaving after five months?” Everything turned out great though, as I eventually became partner at the consulting firm and stayed for 4 years.

During that time, we built websites for governments in Indonesia, Angola and Mongolia and worked with a bunch of city planning and transit agencies all over the US, and traveled for two months out of every year for those 4 years. I would say my experience with that was really great.

Right now, I’m a product designer at a company called Plate IQ.

The product allows restaurants to dive into how much they’re spending on purchases, sort of like what mint.com lets you do for personal finances. We let you know that last month you spent 40% of produce purchases on fancy mushrooms, or that you currently owe half a million dollars in outstanding invoices.

We also can automatically calculate costs for every dish on a menu, letting chefs and owners understand how each ingredient contributes to their bottom line.

In an industry where the margins are already so small, this kind of data is really meaningful for our customers.

Very cool. What have been the most exciting things to you about working in product design and working in tech? What is it about the work that really excites you?

I love product design because I like to build bridges between what a person expects and what technology is able to offer.

I love that I can expect zero to 2 meetings in any given day, and how I can take an idea from concept to completion in sometimes just a few days. It’s a really powerful experience being able to iterate through ideas and develop them so quickly.

Has anything in tech been on the tough side?

Being the only woman on a team can be tough, especially if there are 9 other guys or something, and then there’s you. Even small talk can be awkward if a guy says “I’m working from home today, the wife is sick” and doesn’t think about how that might make you, as a female, feel objectified. “The wife,” like, “the car”? If you have a name for your car, you should definitely have a name for your wife.

One time my friend got reported to HR by someone at work because her “hair flips were too sexy.” Sometimes, I’m just like, are you fucking kidding me?

As someone who didn’t grow up with a ton of money, what is it like seeing Silicon Valley and being in it for so long?

It’s pretty crazy sometimes. I went through a phase where I enjoyed going to all these after parties, hackathons, and conferences. Every tech event had a t-shirt but none were ever made for women, so I collected a bajillion poorly fitting men’s T-shirts in the process, haha.

Sometimes I feel like everyone is patting each other on the back about how good they are at helping startups help startups help other startups, and no one is doing anything meaningful.

That’s me being super cynical, of course. I think there are a lot of companies out here doing great work, fueled by epic rockstar developers and Red Bull. Okay, that’s me being cynical again.

But seriously, startup culture can be amazing. Who honestly wants to work in a real life Office Space? If a startup can make money and provide free meals and unlimited time off and let their employees to go Vegas and Hawaii for team building, that’s awesome.

Yeah—I remember when I first worked in tech—I called it “the underbelly”—the scene of everybody who spent all of their time partying and congratulating each other, verses the ones that weren’t at the parties because they were working on things that really meant something to them. It’s just a funny correlation to me. Another thing that resonated with me in your pre-interview was that—being raised in Iowa—you were taught to be nice, and that you had to unlearn how to be nice when you moved here, which I also went through and it was really hard.

Are you from the Midwest as well?

I’m from North Carolina where it’s like—you’re a nice Southern girl and you say “hi, how are you” to everyone in the grocery stores. And I very quickly—I’m just a cold-hearted human compared to the way that I was when I first got here. I’m curious to hear how it changed for you for that process.

Sure, I actually had a friend tell me last year that I have become more condescending since he met me 9 years ago when I first moved here from Iowa, and that absolutely sucked to hear. And I could totally see how he would feel that way, and I was glad to hear it, and I really thought about it deeply because that’s not the kind of person I want to be.

You also mentioned in your pre-interview that going to Hacker School changed your views on feminism. I’m so curious about that.

Hacker School (now called Recurse Center) was one of the most inclusive working environments I have ever had the privilege of being a part of. The three months I spent in New York really changed how I felt about feminism because I had never before been part of an organization that openly said, “Sexism is not okay here.”

On top of that, the batch of Recurse Center I went to was 40% female, and it was the first time in 6 or 7 years that I was part of anything that was more than 1-5% female. If I had a question, I could ask a guy OR a girl! If I sucked at something, it wasn’t because I was a girl.

That’s huge.

Yeah.

You mentioned another thing in your pre-interview about the concept of self selection, and how you’ve seen it influence hiring of people? I’m curious to hear more of your thoughts on that.

“Culture fit” is such a big thing here. It’s hard to even coach somebody that you think is qualified for a position at a startup on how to pass the culture fit part of an interview in the Bay Area. I would have to know what the culture was like at every single startup and have intimate knowledge of every team at that particular startup to tell you how you need to act if you want to get hired there [chuckles], which is crazy.

I still can’t believe “culture fit” is a term that companies are allowed to use. It seems so obvious that that’s just a bias that is not a positive thing anymore.

Yeah, the problem with using “culture fit” to hire is how easily it can be used to push discriminating practices under the rug. When people have these huge time and budget constraints it’s easier to go with their gut feeling instead of thinking about the real reasons they’re rejecting a candidate. I’ve seen people go the easy route and hire all their friends first, and then everyone else later. “Culture fit” makes it hard to get your foot in the door if you don’t know someone or have an extraordinary ability to market yourself.

It’s complicated because I can see myself hiring people just like me. But that’s what everybody else does too. But there aren’t many like me to start off with, so that’s a problem. Because now all the non-me’s are hiring people not like me.

“The problem with using “culture fit” to hire is how easily it can be used to push discriminating practices under the rug. When people have these huge time and budget constraints it’s easier to go with their gut feeling instead of thinking about the real reasons they’re rejecting a candidate. I’ve seen people go the easy route and hire all their friends first, and then everyone else later. ‘Culture fit’ makes it hard to get your foot in the door if you don’t know someone or have an extraordinary ability to market yourself.”

It’s so complicated. You mentioned also, the importance of finding a champion at work.

I forgot I wrote all these things! I was like, “Was there all that space?” [laughs]

You wrote a lot, but it was really good. You were throwing great stuff at me. 

Yes. I was asking people for advice because I was having trouble at one of my jobs, because I felt like nobody that worked with me was my champion. That person doesn’t have to be trumpeting everything you do, but they should at least be willing to listen to you.

My friend suggested that no matter how good you are at something, if someone opposes you personally, you might as well leave unless you want to play office politics. Honestly if you’re talented, there isn’t any reason you should have to put up with that kind of bullshit. And I mean the passive aggressive, leaving you out of important conversations, denying opportunities kind of bullshit.

At one point in my career, I was told “everyone is a designer these days”, as if it were some trendy thing and I was just jumping on some bandwagon. As much as I respected this person for other reasons, he wasn’t qualified to be the gatekeeper of my career.

So after a bit of thought, I quit that job, became a designer, and haven’t regretted it since.

“My friend suggested that no matter how good you are at something, if someone opposes you personally, you might as well leave unless you want to play office politics. Honestly if you’re talented, there isn’t any reason you should have to put up with that kind of bullshit. And I mean the passive aggressive, leaving you out of important conversations, denying opportunities kind of bullshit.”

And undermines all of your talents and expertise. Yes, that’s frustrating. What do you look for in a job now versus when you started, what is really important to you now?

When I started, I was looking for anything because I was unemployed. So I took any opportunity I could get, whether that was designing a simple, static 5-page website or rolling on a Segway through an ice arena promoting HP photo printers.

Now that I can afford to be picky, I look for problems I think are interesting to solve, and for people who respect me. I think being respected at work is huge and sometimes feels like a luxury, even though it shouldn’t be.

I also look for good listeners. I used to have a manager who would always say “I understand,” but as a way of cutting you off instead of letting you know that he actually understood. I know others who say the same thing, but you can tell they actually listened because they follow up with a relevant comment or question.

Big difference.

Yeah.

I’m so curious, how do you think that your background and the culmination of your life experiences affect how you approach your work?

Hmm. In the beginning I was just grateful for everything that was offered. I never negotiated for more money whenever I had a job just because I was just thankful, but later on I was chatting with a friend and he said he struggled with the same thing because he grew up poor as well. And he said he came to this realization that it’s not wrong to want to grow in order to reach your potential. Why should anyone ever feel sorry about that?

I used to say I was interested in design, and I was interested in working as a designer, but most responses to that had an undertone of, “Oh that’s cute, you’re interested in design. Too bad you’re not a real designer.”

It took me a long time to realize that I wasn’t hurting anyone by being honest instead of modest.

So now I say: “I am good at what I do. I would love to work with you.”

“In the beginning I was just grateful for everything that was offered. I never negotiated for more money whenever I had a job just because I was just thankful, but later on I was chatting with a friend and he said he struggled with the same thing because he grew up poor as well.”

My last question for you would be, what are some of the biggest lessons that you’ve learned that you would give to folks that come from similar backgrounds? What advice would you give to folks that are hoping to get into tech but may not feel like they can?

If you’re still in school, you have SO much time to figure it all out. The technologies and tools will change by the time you graduate anyway, so just focus on learning the fundamentals and building friendships and relationships.

Be genuine, be generous, and tactful. I have never regretted being nice to someone. Rather, my most difficult friendships and relationships were often because I took someone’s generosity for granted or was nasty to the other person for no good reason.

Be thoughtful about your decisions so when there comes a point where you thought you had your dream job and then 6 months in, all you want to do is quit, it’s a decision rather than a reaction. And believe me, this will happen. Startups are crazy like that.

There’s not really one single thing that you can take to heart that will grant you success in every endeavor, but I do think it’s important to ask yourself what you want to achieve. And what is worth giving up to have that?

Early years, how early are we talking?

Where were you born?

I was born in the exotic land of San Jose, just 45 minutes south of here. My parents are Vietnamese, so, I’m Vietnamese-American. San Jose is supposed to be the largest population of Vietnamese outside of Vietnam, I think.

How did you end up in Texas?

My parents moved my brother and I when was 16. I like to say that I’m born and raised in the Bay Area, and then misplaced in Texas. They kind of just gave us a month’s notice before we left. Just, “Oh, and we’re moving to Texas. Pack up your things, say bye to your friends.”

The more interesting version of this story is that my mom followed a monk there. I’m not sure if that’s true, really – that’s what my aunties told me. My mom is incredibly Buddhist, she’s super religious, so it’s completely believable that she followed a monk to Texas. I think the less interesting story is that, financially, it was easier to move to Texas and sustain living there. We moved at a rough time for me and I was pretty distraught. At the time, I had just finished my sophomore year and was coming in as a junior. I was about to be an upperclassman in the food chain of high school. I had found my group of friends and was starting to become stable with my identity. We had such little notice and had to start over in Texas. For a long time, I resented my parents for it and really didn’t understand their decision.

What was it like growing up in conservative Texas after being in California?

The majority of the population in San Jose is Asian and Hispanic, and that’s really all I knew growing up. Coming to Texas, we moved to a small town northwest of Houston. If you drove for 30 minutes, you hit Confederate flags. I experienced culture shock, what I recognize as culture shock, years after. I think what I’ve come to understand, is my place and identity as a daughter of immigrants. San Jose had been full of Vietnamese, and so the culture I carried with me was more easily integrated into my day-to-day. Now, all of a sudden I was in Texas, where many of my common practices and cultural norms felt wholly out of place. It made me very self aware and, for a while, it tormented me. It added complexity to the already difficult experience of being a teenager trying to figure out my own identity. And to this day, I remain consciously aware of my heritage and feel the pressure to carry on those traditions. But I embrace it, and have been learning to balance the two. I speak fluent Vietnamese, I can read and write probably at the level of a kindergartener, and am really happy and somewhat prideful when it comes to sharing traditions.

Eventually, you came back here?

So I’m a designer now. I’m an experience designer at Airbnb. I had always been interested in graphic design. When I was a kid, I loved this virtual pet website, Neopets, and designing “Neopet banners,” which were banners for your pet’s webpage. I started to learn HTML and CSS that way, adding snippets of code to my pet page. And then it grew to designing blogs like Xangas, Myspace, and Livejournals. I was always “revamping my blog”, my angsty teen blog. And then posting about angsty teen things.

Did you have an animated cursor?

Yeah, animated cursor, some marquees, and the Friends theme song that automatically played when you got there. I remember in high school I also loved books, and I had navigated my way through the internet to find maybe five percent off books. I would buy and sell these books, not even making money off of it, probably spending more money than making any, so I could deliver my friends our favorite books with some well designed receipts.

Did you know that you would pursue tech or design as your adult thing?

I always wanted to be a graphic designer. I just loved what I was doing. I eventually started entering crowdsourced competitions. I remember finding 99designs, which is now the bane of existence for designers. But when I was around 17, I would submit logos and win once or twice. And I was like, “$50! I’m going to be rich!” I had always wanted to be a designer, but my parents never really supported arts degrees. And as immigrants they kind of frowned upon it. Now, looking back, I understand, and really respect my parents for having their American Dream, and trying to give me the shortcut to success. I recognize it now, but before it was just, “Why won’t you let me do what I love to do?” They were always pushing the suggestion of more typically successful careers, becoming a doctor, lawyer, something that requires a PhD. My parents frowned upon it so I pursued it on my own.

You pursued it on your own time, and then you ended up doing something totally different in college.

Yeah. I left home at 17. My mom and I had a really rough argument. It had been a struggle with my parents and it was a long time coming. My parents are very traditional and they’re very strict. They kind of pushed suggestions on my behavior, my identity, passions, way of living, and expectations of living. I never felt like I did anything right and I never felt like their expectations of perfection were achievable. I was rebellious, confused about who I was, what I wanted to do, and felt like my own voice didn’t exist with them.

They also had this idea of respect, that when they had their say, even if they were wrong, any sort of response, even a correction through a miscommunication, is considered talking back and disrespectful. This was their definition of respecting elders. Eventually I got tired of having to hold my tongue, and that’s when I became rebellious and defiant.

I’m the eldest. I have a younger brother, and I always say they consider him the golden child. As the oldest, you’re the guinea pig. Whatever you do is always wrong, and they’ll adjust their parenting methods and they will treat my brother better. 

I remember that in my family [chuckles].

Yeah.

It sucks.

You can relate?

Totally. So you bounced?

Yeah. I left early. I forgot the question. Sorry. [laughter]

This is all leading up to college? And doing something different in college than design?

Long story short, I ended up going to school at the University of Houston. I had initially pursued Architecture and then Marketing, looking for a major that would satisfy my love for design, but still would set me off on the right foot in terms of a career. I eventually ended up in Management Information Systems. I thought that since I wasn’t going to study design, I would study something that supplemented it. And through MIS, I studied more coding languages, learned about database architectures, and practiced project management.

And then from there, how did you end up in Silicon Valley?

By that time I had left home, I was already freelancing. I had made logos, built websites, done some branding work. I was also juggling two or three jobs, like hosting and waitressing, trying to sustain myself through college. Instead of finding project management jobs through my major, I would attend the same career fairs, but pitch myself as a designer. I made connections with people who were trying to hire students for project management jobs and ended up designing their websites, or working on their brand and identity. Word of mouth spread and I kept building websites and designing identities for start-ups, corporate companies, and restaurants in Texas. That’s how I started my portfolio.

Since I had moved, all I wanted to do was come back to the Bay. Growing up in Texas, as I established friendships and found my own identity, I recognized what I wanted to do and where I could do it best was where I wanted to be – back in the Bay Area. Getting a job out here was hard. I applied to every design job I could find. I would fly back here pretty often just to attend events and network with people. I had business cards and a resume ready. I had even made a Google Voice phone number with a 650 area code so people would think I lived here, so that the idea of me living elsewhere wouldn’t keep me from getting a job. Each time before I flew out, I did research on companies to find out who was hiring. Then when I got here, I would stop by their offices, drop off my resume, and let them know I was interested in the job.  A lot of times I just cold contacted people. I used LinkedIn to email recruiters, let them know that I was interested in their company, the jobs that they had open, and forwarded them my portfolio and resume. I was turned down or ignored a majority of the time, but ended up landing a job at Playstation.

Awesome. What was your first experiences like working in Silicon Valley?

I had grown up loving video games through my brother, so I was ecstatic when I received the internship offer. I worked as a Web Developer Intern for their Developer Operations. Even after working at companies in Texas, I thought Playstation was incredibly corporate, especially in comparison to today’s tech companies. It was my first introduction to working at a large company and designing for a company whose product I used and admired.

Honestly I wasn’t sure what I had expected. I think I thought it was my dream job. I was given a travel stipend, housing, and it was a paid internship. I made great connections with people in the industry who I still keep in touch with. I really couldn’t have asked for more.

Then, LinkedIn after that?

Not yet. When I had my internship at Playstation I was still in school, but I managed to connect with my professors and was really honest with them. I let them know that I was working and would be absent a lot, wouldn’t be attending a lot of classes either, but I promised that I would catch up on all the lectures, do my homework, and make it to all the exams. After most of the internships had ended at Playstation, I extended my internship for another couple of months and worked there even though school had started. When I came back to school later in the Fall, I got an internship at a design agency in Houston.

I was nearing graduation and had applied at a bunch of jobs at tech companies, with no luck. A friend of one of my co-interns at Playstation worked for LinkedIn referred me there. I remember having a whole week of finals at the time and I hadn’t told the agency I was working for then that I was interviewing. I ducked out, flew out here, and was offered an internship.

It was actually an incredible experience. This was my first time being at a full fledged tech company. I met so so many incredible people with all different kinds of backgrounds and experience. I was offered a full time job on my very last day as an intern. My manager at the time decided not to tell me that I was getting the job and made me worry and scramble for a new job until the very last minute. He decided to tell me the day of, the day that I was leaving, that I got the job.

Oh man.

Yeah! I stayed at LinkedIn for three years. Looking back now, the connections I’ve made, the people that I had met, and just the experience I had were irreplaceable.

And then that leads you to where you are now?

Mm-hmm, yeah.

Awesome. What have been some of the highlights for you, just for your overall tech experience?  

So there are two things. I think the biggest thing that I had learned even from the beginning, flying out here and networking with people, and then working with so many people is that, even though we’re all in tech, everyone has a different story about how they’ve gotten here, what they’re doing, how they’re doing it and why they’re doing it. In the same way that I think you’re interviewing people, it’s just– the people you meet– you’ll never meet the same person twice. I’m constantly blown away and often inspired.

The second thing is being able to learn from everyone and everything. I think not coming from a traditional design background, I feel at a disadvantage. But you learn from being on the job day to day and being around so many talented people. You learn through guidance but also through osmosis, I think, from being around these incredible people. I’m always open to learning and trying new things and I’m so excited that there are endless possibilities and opportunities here.

What have been some of the biggest challenges?

I wouldn’t say the challenges I’ve faced aren’t necessarily caused by tech, but that they’ve been brought into the light through it. I’ve already mentioned that my parents were incredibly traditional and strict. They were tiger parents.

They had me learn every possible skill, hobby, sport. I played tennis, I played piano, swam, Tae Kwon Do, clarinet, basketball, badminton, a million things. They threw every possible skill at my velcro wall of life to see what stuck. I had started piano when I was 4 and played for 18 years.

My parents’ style of teaching and encouragement was through discouragement with an expectation of perfection.

I think one of the things that I remember the most was when I was learning piano, my auntie – my mom’s sister – was my teacher. I was playing a song during a private lesson and I wasn’t doing too well. My family friend, who was also a student and a child prodigy, was also there. My auntie asked me to play it a second time, and this time, have the family friend count how many mistakes I made. And then they asked him to show me how it was supposed to be done and play it correctly. And it was kind of like that all of my life, always being encouraged through discouragement.

Through my upbringing I recognize that I’ve developed self-esteem and self-consciousness issues, where I have this need for reassurance or recognition, whether it be my parents, employers, or managers and I have this need to strive for the utmost perfection.

What I’m constantly learning is that I don’t need to satisfy anybody else’s criteria of whether or not I’m succeeding.

In my experience, I’ve come across personalities that are egotistical, flashing around their title, that would speak from a perspective of authority rather than a place of humility and empathy. And in my self-conscious nature, I’m always cautious, always thinking that I’ve done something wrong. If there was a negative comment I would always think, “Was it me? Was it something I did?” Rather than realizing that it may not be anyone’s fault at all. I always took the blame or I always took it personally. That’s something that I’ve been trying to overcome.

Imposter syndrome is one of the biggest things I recognize in myself. I’m always thinking, “It’s a matter of time. They’re going to find out tomorrow that I’m not exactly as good as I’ve presented myself and that I’m actually not supposed to be here.”

But what I’ve come to acknowledge is that these are things that I’ve actually achieved. I need to take a step back and celebrate my successes and where I’ve gotten, rather than counting all of my misses and what I’ve done wrong. Not only that, but considering those things as stepping stones to getting where I need to go, as points of growth rather than, “This is where I f’d up.”

In tech there is a battle of titles, compensation, experience, all kinds of things. And it’s so easy to feel beaten down by someone else’s ego and to want to compare yourself to them. But I’ve realized that it’s not about me or anyone else, it’s about how I’m doing for myself.

Was there a person or a moment or an event that switched that for you? A kind of epiphany of just like, I don’t have to count my mistakes, I don’t have to worry about these people thinking that I’m not worthy or that I’m not doing it right. Was there a moment where you’re like, “I’m doing fine?”

I don’t think that it was an epiphany really, I think it’s been a long time coming. When I was at LinkedIn, the director of design, now VP of design at LinkedIn, was a mentor to me.

I remember I had really messed up my interview at LinkedIn, I had bombed my interview so badly and I knew it. I had lost my design challenge the morning of my presentation, came late to the interview, frazzled, shirt buttoned incorrectly, like, “Oh my God, I’m so sorry. I messed this up.” I walked through my presentation, my portfolio, and spent the entire day interviewing.

At the end of the afternoon, the director came in, he could tell from my posture – he’s really good at reading body language – he knew I was defeated. He was honest and said bluntly, “I’m going to tell you the truth. I don’t know if the team thinks you’re qualified enough to be full-time on this team. If we do hire you, we’re looking at an internship. If not, I can give you advice on what you can do to improve.”

And I actually really appreciated his honesty. He was straightforward and said, “Let’s just cut the bullshit. Tell me how your day was. Tell me how you feel.” And we just kind of talked through the experience. He told me that it’s either an internship or maybe it won’t work out, but, whatever happened he would personally contact me and give me advice as to what to do next. Three weeks later he gave me a call and told me, “You have an internship. I want you to learn from the team and become better. This is your job to lose.” That’s how he became my mentor and my internship at LinkedIn started.

Through my experiences at LinkedIn, often times I felt like I wasn’t achieving enough, felt beaten down by failures that you inevitably go through. I took that personally as I normally did, and he helped me rationalize my thoughts, made me think objectively. “Did you really do this? How can you improve? These are the right emotions that you’ve gone through. There’s no one to judge you but yourself.” He helped mentor me through my self-esteem and self-consciousness to see my successes and that failures aren’t truly failures. I’m incredibly grateful for that.

What are your biggest motivators? What drives you?

For a while I think I was lost. My biggest goal since I had moved was to come back to the Bay Area. So when I worked for LinkedIn, I had achieved my biggest goal, “I’m back in the San Francisco Bay Area, now what?” And for the longest time I was trying to figure out what’s next for me, my next milestones, and figuring out what I wanted to achieve. I know that I want to leave an impression somehow but how do I do it? I think that’s why I stayed at LinkedIn for a long time, because it was stable, and safe. Familiar.

I think I had finally reached a point at my job there where I felt like it wasn’t enough for me anymore and that I wasn’t growing as much as I wanted to and eventually I moved to my job now, at Airbnb.

For me, I think motivation is, always learning, always feeling challenged and most of all fulfilling my passions, doing things that make me happy and that I’m proud of. That’s what always keeps me going.

What do you think about the state of tech now, in 2016? What excites you? What frustrates you?

I think what we lack sometimes is humility and an awareness for everything but tech. I think taking your experiences in tech and applying it as a perspective and viewpoint to learn is great, but I don’t think that it should be your only perspective. I think both the design and tech scene gets caught up with itself and we forget a world outside of it exists.

I think we foster great opportunities for anyone and everyone and that we have become more self aware of things like diversity and equal opportunity, making it a progressive industry that will only continue forward.

How do you think that your background and life experiences impact the way that you approach your work today?

Thinking through my background and life lessons I have a couple of thoughts:

First—that we’re all imposters. I think we all feel like everyone else thinks we’re a better version of ourselves. I’ve learned to embrace my imposter, celebrate the achievements that make up the identity of my imposter because they are my own achievements.

Second, I’ve decided that perfection doesn’t exist, but I will always strive towards it. Thinking you’re perfect means that you’re accepting that you’ve reached the highest level anyone could ever achieve. That means you’re no longer open to learning and lack humility. I think that striving for perfection means that you’ll always be open to learning, to becoming better.

Lastly, I like to remind myself to do what I’m passionate about and that I’m doing this for myself and not for anyone else.

My last question to you would be, what advice would you give to people from similar backgrounds to you who are hoping to get into tech?

We all have our insecurities. I always think about whether I’ll make it or worry about taking risks and whether or not this is the right time or the right step.

I think my advice is to go for it. Just because you’re taking a risk doesn’t mean you’re going to lose it all. Learning from your failures gives you a better chance the next time you take the risk.

And as an imposter I worry about not having had a background in design and that someone will find me out. I moved to San Francisco just on an internship with LinkedIn, not even a full time job. If I hadn’t done that I don’t think I would have gotten to where I am now.

My advice would be that, take the risk, acknowledge your imposter, succeed from your failures, and do what you love.